Bogdanović, Goran A.

Link to this page

Authority KeyName Variants
orcid::0000-0002-4721-794X
  • Bogdanović, Goran A. (138)
  • Bogdanović, Goran (2)
Projects
Novel Electrochemical and Chemical Methods in Synthesis of Organic Compounds of Interest for Medicine and Material Chemistry Design, synthesis, characterization and assessment of practical applications of coordination and organometallic compounds
Rational design and synthesis of biologically active and coordination compounds and functional materials, relevant for (bio)nanotechnology Synthesis, modeling, physicochemical and biological properties of organic compounds and related metal complexes
Mechanistic studies of the reactions of transition metal ion complexes with biologically relevant molecules Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200122 (University of Kragujevac, Faculty of Science)
Combinatorial libraries of heterogeneous catalysts, natural products, and their derivatives and analogues: the way to biologically active compounds Synthesis, characterization and activity of organic and coordination composition and their application in (bio) nanotechnology
Sinteze, fizičke, strukturne i biološke karakteristike novih kompleksnih jedenjenja Modeling and Numerical Simulations of Complex Many-Body Systems
The study of physicochemical and biochemical processes in living environment that have impacts on pollution and the investigation of possibilities for minimizing the consequences Ministry of Science of the Republic of Montenegro
Characterization and application of fungal metabolites and assessment of new biofungicides potential Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200378 (Institute of Information Technology)
Simultaneous Bioremediation and Soilification of Degraded Areas to Preserve Natural Resources of Biologically Active Substances, and Development and Production of Biomaterials and Dietetic Products Ministry of Education, Science and Technological Development of the Republic of Serbia
Ministry of Science and Technological Development of the Republic of Serbia [142028] BRNS, Mumbai [2006/35/9], Ministry of Science and Technological Development of the Republic of Serbia [142010], DFG [JA466/14-1/2]
Deutsche Forschungsgemeinschaft (DFG) [Ja466/30-1], DFG [Ja466/25-1], University of Dusseldorf DSR [UJ-02-050-DR]
Faculty of Medical Sciences [MP 2014/01] Gaussian program - 1720035
Gaussian program [ON1720035] Humboldt Foundation
Design and modeling of specific features of nanostructured samples Noncovalent interactions of pi-systems and their role in molecular recognition
Molecular determinants of innate immunity in autoimmunity and tumorogenesis Developing infrastructure for priority research fields
Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200168 (University of Belgrade, Faculty of Chemistry) Preclinical investigation of bioactive substances

Author's Bibliography

Rapid access to pyrrolo[3,4-c]quinoline-1,3-diones: An improved synthetic protocol using a precursor prepared by Pfitzinger reaction

Dimitrijević, Marina G.; Bogdanović, Goran A.; Trifunović, Snežana; Joksović, Milan D.

(2023)

TY  - JOUR
AU  - Dimitrijević, Marina G.
AU  - Bogdanović, Goran A.
AU  - Trifunović, Snežana
AU  - Joksović, Milan D.
PY  - 2023
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/10609
AB  - An efficient pTSA-mediated cyclization cascade reaction of Pfitzinger's ester and benzoyl hydrazines has been developed providing a simple procedure for synthesis of pyrrolo [3,4-c]quinoline-1,3-dione derivatives. Unlike traditional synthetic protocol, this method avoids an additional step of conversion of quinoline-3,4-dicarboxylic acids to an anhydride, allowing direct reaction of ester derivative with hydrazine nucleophiles. © 2022 Elsevier Ltd
T2  - Tetrahedron
T1  - Rapid access to pyrrolo[3,4-c]quinoline-1,3-diones: An improved synthetic protocol using a precursor prepared by Pfitzinger reaction
DO  - 10.1016/j.tet.2022.133236
ER  - 
@article{
author = "Dimitrijević, Marina G. and Bogdanović, Goran A. and Trifunović, Snežana and Joksović, Milan D.",
year = "2023",
abstract = "An efficient pTSA-mediated cyclization cascade reaction of Pfitzinger's ester and benzoyl hydrazines has been developed providing a simple procedure for synthesis of pyrrolo [3,4-c]quinoline-1,3-dione derivatives. Unlike traditional synthetic protocol, this method avoids an additional step of conversion of quinoline-3,4-dicarboxylic acids to an anhydride, allowing direct reaction of ester derivative with hydrazine nucleophiles. © 2022 Elsevier Ltd",
journal = "Tetrahedron",
title = "Rapid access to pyrrolo[3,4-c]quinoline-1,3-diones: An improved synthetic protocol using a precursor prepared by Pfitzinger reaction",
doi = "10.1016/j.tet.2022.133236"
}
Dimitrijević, M. G., Bogdanović, G. A., Trifunović, S.,& Joksović, M. D.. (2023). Rapid access to pyrrolo[3,4-c]quinoline-1,3-diones: An improved synthetic protocol using a precursor prepared by Pfitzinger reaction. in Tetrahedron.
https://doi.org/10.1016/j.tet.2022.133236
Dimitrijević MG, Bogdanović GA, Trifunović S, Joksović MD. Rapid access to pyrrolo[3,4-c]quinoline-1,3-diones: An improved synthetic protocol using a precursor prepared by Pfitzinger reaction. in Tetrahedron. 2023;.
doi:10.1016/j.tet.2022.133236 .
Dimitrijević, Marina G., Bogdanović, Goran A., Trifunović, Snežana, Joksović, Milan D., "Rapid access to pyrrolo[3,4-c]quinoline-1,3-diones: An improved synthetic protocol using a precursor prepared by Pfitzinger reaction" in Tetrahedron (2023),
https://doi.org/10.1016/j.tet.2022.133236 . .

Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction

Stevanović, Dragana D.; Bugarinović, Jovana; Pešić, Marko; Todosijević, Anka; Bogdanović, Goran A.; Damljanović, Ivan S.

(2021)

TY  - JOUR
AU  - Stevanović, Dragana D.
AU  - Bugarinović, Jovana
AU  - Pešić, Marko
AU  - Todosijević, Anka
AU  - Bogdanović, Goran A.
AU  - Damljanović, Ivan S.
PY  - 2021
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/10070
AB  - A simple protocol has been developed for the chemoselective synthesis of ferrocene-containing Rauhut–Currier adducts from 1-ferrocenyl-2-nitroethene and vinyl ketones using 20 mol% of triphenylphosphine. Multifunctional ferrocene derivatives were obtained in moderate to high yields (51–92%) by the coupling between the α-position of vinyl ketones and the β-position of the nitroalkene. The study of the Rauhut–Currier reaction under the described conditions showed that the strong electron-donating group at the β-position of nitroalkenes plays a significant role in the reaction outcome due to prevention of polymerization and stabilization of the zwitterionic intermediate. Additionally, a preparative synthesis of 4-ferrocenyl-3-methylene-5-nitropentan-2-one was carried out and its synthetic transformations showed easy conversion to other useful building blocks.
T2  - RSC Advances
T1  - Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction
VL  - 11
IS  - 57
SP  - 36208
EP  - 36214
DO  - 10.1039/D1RA07619A
ER  - 
@article{
author = "Stevanović, Dragana D. and Bugarinović, Jovana and Pešić, Marko and Todosijević, Anka and Bogdanović, Goran A. and Damljanović, Ivan S.",
year = "2021",
abstract = "A simple protocol has been developed for the chemoselective synthesis of ferrocene-containing Rauhut–Currier adducts from 1-ferrocenyl-2-nitroethene and vinyl ketones using 20 mol% of triphenylphosphine. Multifunctional ferrocene derivatives were obtained in moderate to high yields (51–92%) by the coupling between the α-position of vinyl ketones and the β-position of the nitroalkene. The study of the Rauhut–Currier reaction under the described conditions showed that the strong electron-donating group at the β-position of nitroalkenes plays a significant role in the reaction outcome due to prevention of polymerization and stabilization of the zwitterionic intermediate. Additionally, a preparative synthesis of 4-ferrocenyl-3-methylene-5-nitropentan-2-one was carried out and its synthetic transformations showed easy conversion to other useful building blocks.",
journal = "RSC Advances",
title = "Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction",
volume = "11",
number = "57",
pages = "36208-36214",
doi = "10.1039/D1RA07619A"
}
Stevanović, D. D., Bugarinović, J., Pešić, M., Todosijević, A., Bogdanović, G. A.,& Damljanović, I. S.. (2021). Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction. in RSC Advances, 11(57), 36208-36214.
https://doi.org/10.1039/D1RA07619A
Stevanović DD, Bugarinović J, Pešić M, Todosijević A, Bogdanović GA, Damljanović IS. Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction. in RSC Advances. 2021;11(57):36208-36214.
doi:10.1039/D1RA07619A .
Stevanović, Dragana D., Bugarinović, Jovana, Pešić, Marko, Todosijević, Anka, Bogdanović, Goran A., Damljanović, Ivan S., "Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut–Currier reaction" in RSC Advances, 11, no. 57 (2021):36208-36214,
https://doi.org/10.1039/D1RA07619A . .
2
2

On water synthesis of the novel 2-oxo-1,2,3,4-tetrahydropyrimidines

Milović, Emilija; Janković, Nenad Ž.; Bogdanović, Goran A.; Petronijević, Jelena; Joksimović, Nenad

(2021)

TY  - JOUR
AU  - Milović, Emilija
AU  - Janković, Nenad Ž.
AU  - Bogdanović, Goran A.
AU  - Petronijević, Jelena
AU  - Joksimović, Nenad
PY  - 2021
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9754
AB  - A simple on water approach for the synthesis of novel tetrahydropyrimidine (THPM) derivatives has been developed under a green and sustainable fashion. For the first time, a deuterated Biginelli's hybrid was synthesized. Novel THPMs are suitable for further derivatization and could be an excellent toolkit for lead-oriented synthesis and/or cross-coupling reactions. (C) 2020 Elsevier Ltd. All rights reserved.
T2  - Tetrahedron
T1  - On water synthesis of the novel 2-oxo-1,2,3,4-tetrahydropyrimidines
VL  - 78
SP  - 131790
DO  - 10.1016/j.tet.2020.131790
ER  - 
@article{
author = "Milović, Emilija and Janković, Nenad Ž. and Bogdanović, Goran A. and Petronijević, Jelena and Joksimović, Nenad",
year = "2021",
abstract = "A simple on water approach for the synthesis of novel tetrahydropyrimidine (THPM) derivatives has been developed under a green and sustainable fashion. For the first time, a deuterated Biginelli's hybrid was synthesized. Novel THPMs are suitable for further derivatization and could be an excellent toolkit for lead-oriented synthesis and/or cross-coupling reactions. (C) 2020 Elsevier Ltd. All rights reserved.",
journal = "Tetrahedron",
title = "On water synthesis of the novel 2-oxo-1,2,3,4-tetrahydropyrimidines",
volume = "78",
pages = "131790",
doi = "10.1016/j.tet.2020.131790"
}
Milović, E., Janković, N. Ž., Bogdanović, G. A., Petronijević, J.,& Joksimović, N.. (2021). On water synthesis of the novel 2-oxo-1,2,3,4-tetrahydropyrimidines. in Tetrahedron, 78, 131790.
https://doi.org/10.1016/j.tet.2020.131790
Milović E, Janković NŽ, Bogdanović GA, Petronijević J, Joksimović N. On water synthesis of the novel 2-oxo-1,2,3,4-tetrahydropyrimidines. in Tetrahedron. 2021;78:131790.
doi:10.1016/j.tet.2020.131790 .
Milović, Emilija, Janković, Nenad Ž., Bogdanović, Goran A., Petronijević, Jelena, Joksimović, Nenad, "On water synthesis of the novel 2-oxo-1,2,3,4-tetrahydropyrimidines" in Tetrahedron, 78 (2021):131790,
https://doi.org/10.1016/j.tet.2020.131790 . .
5
4

Electronic Supplementary Information (ESI) : Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut-Currier reaction

Stevanović, Dragana D.; Bugarinović, Jovana; Pešić, Marko; Todosijević, Anka; Bogdanović, Goran A.; Damljanović, Ivan S.

(2021)

TY  - DATA
AU  - Stevanović, Dragana D.
AU  - Bugarinović, Jovana
AU  - Pešić, Marko
AU  - Todosijević, Anka
AU  - Bogdanović, Goran A.
AU  - Damljanović, Ivan S.
PY  - 2021
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/10085
AB  - Electronic supplementary information (ESI) available: Detailed experimental procedures, spectral characterisation (including copies of 1H and 13C NMR spectra) of all new compounds, crystallographic data and CIF file. CCDC 2095955. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/D1RA07619A
T2  - RSC Advances
T1  - Electronic Supplementary Information (ESI) : Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut-Currier reaction
VL  - 11
IS  - 57
SP  - S1
EP  - S43
DO  - 10.1039/D1RA07619A
ER  - 
@misc{
author = "Stevanović, Dragana D. and Bugarinović, Jovana and Pešić, Marko and Todosijević, Anka and Bogdanović, Goran A. and Damljanović, Ivan S.",
year = "2021",
abstract = "Electronic supplementary information (ESI) available: Detailed experimental procedures, spectral characterisation (including copies of 1H and 13C NMR spectra) of all new compounds, crystallographic data and CIF file. CCDC 2095955. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/D1RA07619A",
journal = "RSC Advances",
title = "Electronic Supplementary Information (ESI) : Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut-Currier reaction",
volume = "11",
number = "57",
pages = "S1-S43",
doi = "10.1039/D1RA07619A"
}
Stevanović, D. D., Bugarinović, J., Pešić, M., Todosijević, A., Bogdanović, G. A.,& Damljanović, I. S.. (2021). Electronic Supplementary Information (ESI) : Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut-Currier reaction. in RSC Advances, 11(57), S1-S43.
https://doi.org/10.1039/D1RA07619A
Stevanović DD, Bugarinović J, Pešić M, Todosijević A, Bogdanović GA, Damljanović IS. Electronic Supplementary Information (ESI) : Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut-Currier reaction. in RSC Advances. 2021;11(57):S1-S43.
doi:10.1039/D1RA07619A .
Stevanović, Dragana D., Bugarinović, Jovana, Pešić, Marko, Todosijević, Anka, Bogdanović, Goran A., Damljanović, Ivan S., "Electronic Supplementary Information (ESI) : Chemoselective synthesis of multifunctional ferrocene-containing derivatives by the cross Rauhut-Currier reaction" in RSC Advances, 11, no. 57 (2021):S1-S43,
https://doi.org/10.1039/D1RA07619A . .
2

CCDC 2095955: Experimental Crystal Structure Determination

Stevanović, Dragana D.; Bugarinović, Jovana; Pešić, Marko; Todosijević, Anka; Bogdanović, Goran A.; Damljanović, Ivan S.

(2021)

TY  - DATA
AU  - Stevanović, Dragana D.
AU  - Bugarinović, Jovana
AU  - Pešić, Marko
AU  - Todosijević, Anka
AU  - Bogdanović, Goran A.
AU  - Damljanović, Ivan S.
PY  - 2021
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/10086
AB  - ZAQGIL : 1,3-Diferrocenyl-2-methylene-4-nitrobutan-1-one Space Group: P 1 (2), Cell: a 5.89550(10)Å b 12.6957(3)Å c 15.6399(4)Å, α 66.206(2)° β 86.515(2)° γ 80.988(2)°
T2  - CCDC
T1  - CCDC 2095955: Experimental Crystal Structure Determination
DO  - 10.5517/ccdc.csd.cc28c0g4
ER  - 
@misc{
author = "Stevanović, Dragana D. and Bugarinović, Jovana and Pešić, Marko and Todosijević, Anka and Bogdanović, Goran A. and Damljanović, Ivan S.",
year = "2021",
abstract = "ZAQGIL : 1,3-Diferrocenyl-2-methylene-4-nitrobutan-1-one Space Group: P 1 (2), Cell: a 5.89550(10)Å b 12.6957(3)Å c 15.6399(4)Å, α 66.206(2)° β 86.515(2)° γ 80.988(2)°",
journal = "CCDC",
title = "CCDC 2095955: Experimental Crystal Structure Determination",
doi = "10.5517/ccdc.csd.cc28c0g4"
}
Stevanović, D. D., Bugarinović, J., Pešić, M., Todosijević, A., Bogdanović, G. A.,& Damljanović, I. S.. (2021). CCDC 2095955: Experimental Crystal Structure Determination. in CCDC.
https://doi.org/10.5517/ccdc.csd.cc28c0g4
Stevanović DD, Bugarinović J, Pešić M, Todosijević A, Bogdanović GA, Damljanović IS. CCDC 2095955: Experimental Crystal Structure Determination. in CCDC. 2021;.
doi:10.5517/ccdc.csd.cc28c0g4 .
Stevanović, Dragana D., Bugarinović, Jovana, Pešić, Marko, Todosijević, Anka, Bogdanović, Goran A., Damljanović, Ivan S., "CCDC 2095955: Experimental Crystal Structure Determination" in CCDC (2021),
https://doi.org/10.5517/ccdc.csd.cc28c0g4 . .

Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas

Minić, Aleksandra; Novaković, Slađana B.; Bogdanović, Goran A.; Bugarinović, Jovana P.; Pešić, Marko S.; Todosijević, Anka; Ilić-Komatina, Danijela; Damljanović, Ivan S.; Stevanović, Dragana D.

(2020)

TY  - JOUR
AU  - Minić, Aleksandra
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Bugarinović, Jovana P.
AU  - Pešić, Marko S.
AU  - Todosijević, Anka
AU  - Ilić-Komatina, Danijela
AU  - Damljanović, Ivan S.
AU  - Stevanović, Dragana D.
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8808
AB  - The stereochemical phenomenon that arises from hindered rotation around bonds in nonplanar molecules is termed the atropoisomerism. During our previous work we noted the presence of this kind of isomerism in 1-aryl-4-ferrocenyl-3-phenyltetrahydropyrimidin-2(1H)-ones obtained from ortho-substituted 3-(arylamino)-1-ferrocenylpropan-1-ols. Inspired by an interesting biological/medical features of six-membered cyclic ureas and characteristic of “atropoisomers - things that rotate”, herein we present an easy performable synthesis and full characterisation of novel atropoisomeric ferrocene-containing six-membered cyclic ureas. In addition, we successfully determined the crystal structure of two atropoisomers for the same compound. Molecular structural properties and intermolecular interactions of these two structures have been compared and analyzed in detail. Interesting, it has been found that these two isomers although quite similar in conformation and geometrical parameters, form very different crystal packing. © 2019 Elsevier Ltd
T2  - Polyhedron
T1  - Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas
VL  - 177
SP  - 114316
DO  - 10.1016/j.poly.2019.114316
ER  - 
@article{
author = "Minić, Aleksandra and Novaković, Slađana B. and Bogdanović, Goran A. and Bugarinović, Jovana P. and Pešić, Marko S. and Todosijević, Anka and Ilić-Komatina, Danijela and Damljanović, Ivan S. and Stevanović, Dragana D.",
year = "2020",
abstract = "The stereochemical phenomenon that arises from hindered rotation around bonds in nonplanar molecules is termed the atropoisomerism. During our previous work we noted the presence of this kind of isomerism in 1-aryl-4-ferrocenyl-3-phenyltetrahydropyrimidin-2(1H)-ones obtained from ortho-substituted 3-(arylamino)-1-ferrocenylpropan-1-ols. Inspired by an interesting biological/medical features of six-membered cyclic ureas and characteristic of “atropoisomers - things that rotate”, herein we present an easy performable synthesis and full characterisation of novel atropoisomeric ferrocene-containing six-membered cyclic ureas. In addition, we successfully determined the crystal structure of two atropoisomers for the same compound. Molecular structural properties and intermolecular interactions of these two structures have been compared and analyzed in detail. Interesting, it has been found that these two isomers although quite similar in conformation and geometrical parameters, form very different crystal packing. © 2019 Elsevier Ltd",
journal = "Polyhedron",
title = "Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas",
volume = "177",
pages = "114316",
doi = "10.1016/j.poly.2019.114316"
}
Minić, A., Novaković, S. B., Bogdanović, G. A., Bugarinović, J. P., Pešić, M. S., Todosijević, A., Ilić-Komatina, D., Damljanović, I. S.,& Stevanović, D. D.. (2020). Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas. in Polyhedron, 177, 114316.
https://doi.org/10.1016/j.poly.2019.114316
Minić A, Novaković SB, Bogdanović GA, Bugarinović JP, Pešić MS, Todosijević A, Ilić-Komatina D, Damljanović IS, Stevanović DD. Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas. in Polyhedron. 2020;177:114316.
doi:10.1016/j.poly.2019.114316 .
Minić, Aleksandra, Novaković, Slađana B., Bogdanović, Goran A., Bugarinović, Jovana P., Pešić, Marko S., Todosijević, Anka, Ilić-Komatina, Danijela, Damljanović, Ivan S., Stevanović, Dragana D., "Synthesis and structural characterizations of novel atropoisomeric ferrocene-containing six-membered cyclic ureas" in Polyhedron, 177 (2020):114316,
https://doi.org/10.1016/j.poly.2019.114316 . .
1
8
1
6

Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines

Pešić, Marko; Bugarinović, Jovana; Minić, Aleksandra; Bogdanović, Goran A.; Todosijević, Anka; Stevanović, Dragana D.; Damljanović, Ivan S.

(2020)

TY  - JOUR
AU  - Pešić, Marko
AU  - Bugarinović, Jovana
AU  - Minić, Aleksandra
AU  - Bogdanović, Goran A.
AU  - Todosijević, Anka
AU  - Stevanović, Dragana D.
AU  - Damljanović, Ivan S.
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8892
AB  - The design, synthesis, spectral and electrochemical characterization of a series of novel pyrrolidine derivatives have been described. The synthesis was achieved by 1,3-dipolar cycloaddition of azomethine ylides and ferrocene-substituted chalcones, while detailed characterization of the compounds was performed by IR, NMR and elemental analyses, followed by X-ray diffraction experiment for one representative. The electrochemical properties of obtained ferrocene-containing heterocycles were examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). These techniques revealed the quasi-reversible one-electron oxidation process. DNA-binding capacity of all products was studied using CV and DPV, highlighting a derivative with five times better binding affinity than the others. DFT calculations and molecular docking studies were carried out to gain more exhaustive insight into the type of interactions of the distinguished compound and the nucleic acid.
T2  - Journal of The Electrochemical Society
T1  - Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines
VL  - 167
IS  - 2
SP  - 025502
DO  - 10.1149/1945-7111/ab68cc
ER  - 
@article{
author = "Pešić, Marko and Bugarinović, Jovana and Minić, Aleksandra and Bogdanović, Goran A. and Todosijević, Anka and Stevanović, Dragana D. and Damljanović, Ivan S.",
year = "2020",
abstract = "The design, synthesis, spectral and electrochemical characterization of a series of novel pyrrolidine derivatives have been described. The synthesis was achieved by 1,3-dipolar cycloaddition of azomethine ylides and ferrocene-substituted chalcones, while detailed characterization of the compounds was performed by IR, NMR and elemental analyses, followed by X-ray diffraction experiment for one representative. The electrochemical properties of obtained ferrocene-containing heterocycles were examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). These techniques revealed the quasi-reversible one-electron oxidation process. DNA-binding capacity of all products was studied using CV and DPV, highlighting a derivative with five times better binding affinity than the others. DFT calculations and molecular docking studies were carried out to gain more exhaustive insight into the type of interactions of the distinguished compound and the nucleic acid.",
journal = "Journal of The Electrochemical Society",
title = "Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines",
volume = "167",
number = "2",
pages = "025502",
doi = "10.1149/1945-7111/ab68cc"
}
Pešić, M., Bugarinović, J., Minić, A., Bogdanović, G. A., Todosijević, A., Stevanović, D. D.,& Damljanović, I. S.. (2020). Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines. in Journal of The Electrochemical Society, 167(2), 025502.
https://doi.org/10.1149/1945-7111/ab68cc
Pešić M, Bugarinović J, Minić A, Bogdanović GA, Todosijević A, Stevanović DD, Damljanović IS. Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines. in Journal of The Electrochemical Society. 2020;167(2):025502.
doi:10.1149/1945-7111/ab68cc .
Pešić, Marko, Bugarinović, Jovana, Minić, Aleksandra, Bogdanović, Goran A., Todosijević, Anka, Stevanović, Dragana D., Damljanović, Ivan S., "Synthesis and Electrochemical Estimation of DNA-Binding Capacity of Novel Ferrocene-Containing Pyrrolidines" in Journal of The Electrochemical Society, 167, no. 2 (2020):025502,
https://doi.org/10.1149/1945-7111/ab68cc . .
1
1
1

Electrochemical characterization and estimation of DNA-binding capacity of a series of novel ferrocene derivatives

Pešić, Marko S.; Bugarinović, Jovana P.; Minić, Aleksandra; Novaković, Slađana B.; Bogdanović, Goran A.; Todosijević, Anka; Stevanović, Dragana D.; Damljanović, Ivan S.

(2020)

TY  - JOUR
AU  - Pešić, Marko S.
AU  - Bugarinović, Jovana P.
AU  - Minić, Aleksandra
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Todosijević, Anka
AU  - Stevanović, Dragana D.
AU  - Damljanović, Ivan S.
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8784
AB  - The synthesis of a series of methyl 2-alkyl-5-aryl-4-ferrocenoylpyrrolidine-2-carboxylates has been achieved by [3 + 2] dipolar cycloaddition of azomethine ylides to acryloylferrocene. The electrochemical properties of novel products were examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). These techniques revealed the quasi-reversible one-electron oxidation process. The DNA-binding capacity of all the products was also studied using CV and DPV, and significant interactions between synthesized compounds and nucleic acid, mostly of the electrostatic type, were disclosed. DFT calculations and molecular docking tests were carried out to gain a more exhaustive insight into the interactions of the obtained products with nucleic acid. A detailed characterization of the new compounds was performed by IR, NMR and elemental analyses, followed by single-crystal X-ray diffraction experiments for two representatives. © 2019 Elsevier B.V.
T2  - Bioelectrochemistry
T1  - Electrochemical characterization and estimation of DNA-binding capacity of a series of novel ferrocene derivatives
VL  - 132
SP  - 107412
DO  - 10.1016/j.bioelechem.2019.107412
ER  - 
@article{
author = "Pešić, Marko S. and Bugarinović, Jovana P. and Minić, Aleksandra and Novaković, Slađana B. and Bogdanović, Goran A. and Todosijević, Anka and Stevanović, Dragana D. and Damljanović, Ivan S.",
year = "2020",
abstract = "The synthesis of a series of methyl 2-alkyl-5-aryl-4-ferrocenoylpyrrolidine-2-carboxylates has been achieved by [3 + 2] dipolar cycloaddition of azomethine ylides to acryloylferrocene. The electrochemical properties of novel products were examined by cyclic voltammetry (CV) and differential pulse voltammetry (DPV). These techniques revealed the quasi-reversible one-electron oxidation process. The DNA-binding capacity of all the products was also studied using CV and DPV, and significant interactions between synthesized compounds and nucleic acid, mostly of the electrostatic type, were disclosed. DFT calculations and molecular docking tests were carried out to gain a more exhaustive insight into the interactions of the obtained products with nucleic acid. A detailed characterization of the new compounds was performed by IR, NMR and elemental analyses, followed by single-crystal X-ray diffraction experiments for two representatives. © 2019 Elsevier B.V.",
journal = "Bioelectrochemistry",
title = "Electrochemical characterization and estimation of DNA-binding capacity of a series of novel ferrocene derivatives",
volume = "132",
pages = "107412",
doi = "10.1016/j.bioelechem.2019.107412"
}
Pešić, M. S., Bugarinović, J. P., Minić, A., Novaković, S. B., Bogdanović, G. A., Todosijević, A., Stevanović, D. D.,& Damljanović, I. S.. (2020). Electrochemical characterization and estimation of DNA-binding capacity of a series of novel ferrocene derivatives. in Bioelectrochemistry, 132, 107412.
https://doi.org/10.1016/j.bioelechem.2019.107412
Pešić MS, Bugarinović JP, Minić A, Novaković SB, Bogdanović GA, Todosijević A, Stevanović DD, Damljanović IS. Electrochemical characterization and estimation of DNA-binding capacity of a series of novel ferrocene derivatives. in Bioelectrochemistry. 2020;132:107412.
doi:10.1016/j.bioelechem.2019.107412 .
Pešić, Marko S., Bugarinović, Jovana P., Minić, Aleksandra, Novaković, Slađana B., Bogdanović, Goran A., Todosijević, Anka, Stevanović, Dragana D., Damljanović, Ivan S., "Electrochemical characterization and estimation of DNA-binding capacity of a series of novel ferrocene derivatives" in Bioelectrochemistry, 132 (2020):107412,
https://doi.org/10.1016/j.bioelechem.2019.107412 . .
19
10
18

Crystal structure of ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate, C7H7F3N2O2

Jaćimović, Željko. K; Novaković, Slađana B.; Bogdanović, Goran A.; Kosović, Milica; Libowitzky, Eugen; Giester, Gerald

(2020)

TY  - JOUR
AU  - Jaćimović, Željko. K
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Kosović, Milica
AU  - Libowitzky, Eugen
AU  - Giester, Gerald
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9065
AB  - C7H7F3N2O2, monoclinic, P21/m (no. 11), a = 6.8088(8) Å, b = 6.7699(9) Å, c = 9.9351(12) Å, β = 105.416(3)°, V = 441.48(9) Å 3 , Z = 2, R gt ( F ) = 0.0398, wR ref ( F 2 ) = 0.1192, T = 200(2) K.
T2  - Zeitschrift für Kristallographie - New Crystal Structures
T1  - Crystal structure of ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate, C7H7F3N2O2
VL  - 235
IS  - 5
SP  - 1189
EP  - 1190
DO  - 10.1515/ncrs-2020-0242
ER  - 
@article{
author = "Jaćimović, Željko. K and Novaković, Slađana B. and Bogdanović, Goran A. and Kosović, Milica and Libowitzky, Eugen and Giester, Gerald",
year = "2020",
abstract = "C7H7F3N2O2, monoclinic, P21/m (no. 11), a = 6.8088(8) Å, b = 6.7699(9) Å, c = 9.9351(12) Å, β = 105.416(3)°, V = 441.48(9) Å 3 , Z = 2, R gt ( F ) = 0.0398, wR ref ( F 2 ) = 0.1192, T = 200(2) K.",
journal = "Zeitschrift für Kristallographie - New Crystal Structures",
title = "Crystal structure of ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate, C7H7F3N2O2",
volume = "235",
number = "5",
pages = "1189-1190",
doi = "10.1515/ncrs-2020-0242"
}
Jaćimović, Željko. K., Novaković, S. B., Bogdanović, G. A., Kosović, M., Libowitzky, E.,& Giester, G.. (2020). Crystal structure of ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate, C7H7F3N2O2. in Zeitschrift für Kristallographie - New Crystal Structures, 235(5), 1189-1190.
https://doi.org/10.1515/ncrs-2020-0242
Jaćimović ŽK, Novaković SB, Bogdanović GA, Kosović M, Libowitzky E, Giester G. Crystal structure of ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate, C7H7F3N2O2. in Zeitschrift für Kristallographie - New Crystal Structures. 2020;235(5):1189-1190.
doi:10.1515/ncrs-2020-0242 .
Jaćimović, Željko. K, Novaković, Slađana B., Bogdanović, Goran A., Kosović, Milica, Libowitzky, Eugen, Giester, Gerald, "Crystal structure of ethyl 3-(trifluoromethyl)-1H-pyrazole-4-carboxylate, C7H7F3N2O2" in Zeitschrift für Kristallographie - New Crystal Structures, 235, no. 5 (2020):1189-1190,
https://doi.org/10.1515/ncrs-2020-0242 . .
3
1

Synthesis, structural and electrochemical characterization of novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones

Minić, Aleksandra; Pešić, Marko S; Novaković, Slađana B.; Bogdanović, Goran A.; Todosijević, Anka; Ilić-Komatina, Danijela; Stevanović, Dragana D.

(2020)

TY  - JOUR
AU  - Minić, Aleksandra
AU  - Pešić, Marko S
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Todosijević, Anka
AU  - Ilić-Komatina, Danijela
AU  - Stevanović, Dragana D.
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9119
AB  - Herein, we report an easy performable method for the synthesis of ferrocene-containing tetrahydropyrimidin-2(1H)-ones starting from the corresponding 3-arylamino-1-ferrocenylpropan-1-ols and sodium cyanate (NaOCN) in the presence of glacial acetic acid. The protocol is included an intramolecular cyclization of an in situ generated 1,3-hydroxyurea. The scope of the reaction towards eleven ferrocene-containing 1,3-amino alcohols has been explored and the targeted 1-aryl-4-ferrocenyltetrahidropyrimidin-2(1H)-ones were obtained in good to high yields (up to 93%). All products have been isolated in high purity >95%. In addition, we have provided a detailed structural characterization of the new compounds, which has been performed by IR and NMR spectroscopy. The single-crystal X-ray diffraction analysis was successfully performed on three representative examples, as well as elemental analysis. Moreover, molecular structure properties and intermolecular interactions of these three structures have been compared and analyzed in detail. Electrochemical properties of products were investigated by cyclic voltammetry. This investigation revealed the quasi-reversible one-electron redox process.
T2  - Journal of Organometallic Chemistry
T1  - Synthesis, structural and electrochemical characterization of novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones
VL  - 923
SP  - 121422
DO  - 10.1016/j.jorganchem.2020.121422
ER  - 
@article{
author = "Minić, Aleksandra and Pešić, Marko S and Novaković, Slađana B. and Bogdanović, Goran A. and Todosijević, Anka and Ilić-Komatina, Danijela and Stevanović, Dragana D.",
year = "2020",
abstract = "Herein, we report an easy performable method for the synthesis of ferrocene-containing tetrahydropyrimidin-2(1H)-ones starting from the corresponding 3-arylamino-1-ferrocenylpropan-1-ols and sodium cyanate (NaOCN) in the presence of glacial acetic acid. The protocol is included an intramolecular cyclization of an in situ generated 1,3-hydroxyurea. The scope of the reaction towards eleven ferrocene-containing 1,3-amino alcohols has been explored and the targeted 1-aryl-4-ferrocenyltetrahidropyrimidin-2(1H)-ones were obtained in good to high yields (up to 93%). All products have been isolated in high purity >95%. In addition, we have provided a detailed structural characterization of the new compounds, which has been performed by IR and NMR spectroscopy. The single-crystal X-ray diffraction analysis was successfully performed on three representative examples, as well as elemental analysis. Moreover, molecular structure properties and intermolecular interactions of these three structures have been compared and analyzed in detail. Electrochemical properties of products were investigated by cyclic voltammetry. This investigation revealed the quasi-reversible one-electron redox process.",
journal = "Journal of Organometallic Chemistry",
title = "Synthesis, structural and electrochemical characterization of novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones",
volume = "923",
pages = "121422",
doi = "10.1016/j.jorganchem.2020.121422"
}
Minić, A., Pešić, M. S., Novaković, S. B., Bogdanović, G. A., Todosijević, A., Ilić-Komatina, D.,& Stevanović, D. D.. (2020). Synthesis, structural and electrochemical characterization of novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones. in Journal of Organometallic Chemistry, 923, 121422.
https://doi.org/10.1016/j.jorganchem.2020.121422
Minić A, Pešić MS, Novaković SB, Bogdanović GA, Todosijević A, Ilić-Komatina D, Stevanović DD. Synthesis, structural and electrochemical characterization of novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones. in Journal of Organometallic Chemistry. 2020;923:121422.
doi:10.1016/j.jorganchem.2020.121422 .
Minić, Aleksandra, Pešić, Marko S, Novaković, Slađana B., Bogdanović, Goran A., Todosijević, Anka, Ilić-Komatina, Danijela, Stevanović, Dragana D., "Synthesis, structural and electrochemical characterization of novel ferrocene-containing tetrahydropyrimidin-2(1H)-ones" in Journal of Organometallic Chemistry, 923 (2020):121422,
https://doi.org/10.1016/j.jorganchem.2020.121422 . .
4
1
3

Green synthesis of benzamide-dioxoisoindoline derivatives and assessment of their radical scavenging activity – Experimental and theoretical approach

Milovanović, Vesna M; Petrović, Zorica D.; Novaković, Slađana B.; Bogdanović, Goran A.; Petrović, Vladimir P.; Simijonović, Dušica

(2020)

TY  - JOUR
AU  - Milovanović, Vesna M
AU  - Petrović, Zorica D.
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Petrović, Vladimir P.
AU  - Simijonović, Dušica
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9123
AB  - A series of benzamide-dioxoisoindoline derivatives 3 was obtained, starting from phthalic anhydride and different benzoyl hydrazides 2, by ultrasound irradiation in water as solvent and without any catalyst. Five obtained compounds have been reported in this study for the first time and crystal structure of compound 3h was determined. All compounds were subjected to experimental determination of their antioxidative potential. DPPH test revealed that newly synthesized phenolic compounds 3d, 3e, and 3j are the best antioxidants. Additionally, probable radical scavenging pathway was analysed for reactions of the most active compounds and some radicals that can be found in living cells.
T2  - Tetrahedron
T1  - Green synthesis of benzamide-dioxoisoindoline derivatives and assessment of their radical scavenging activity – Experimental and theoretical approach
VL  - 76
IS  - 38
SP  - 131456
DO  - 10.1016/j.tet.2020.131456
ER  - 
@article{
author = "Milovanović, Vesna M and Petrović, Zorica D. and Novaković, Slađana B. and Bogdanović, Goran A. and Petrović, Vladimir P. and Simijonović, Dušica",
year = "2020",
abstract = "A series of benzamide-dioxoisoindoline derivatives 3 was obtained, starting from phthalic anhydride and different benzoyl hydrazides 2, by ultrasound irradiation in water as solvent and without any catalyst. Five obtained compounds have been reported in this study for the first time and crystal structure of compound 3h was determined. All compounds were subjected to experimental determination of their antioxidative potential. DPPH test revealed that newly synthesized phenolic compounds 3d, 3e, and 3j are the best antioxidants. Additionally, probable radical scavenging pathway was analysed for reactions of the most active compounds and some radicals that can be found in living cells.",
journal = "Tetrahedron",
title = "Green synthesis of benzamide-dioxoisoindoline derivatives and assessment of their radical scavenging activity – Experimental and theoretical approach",
volume = "76",
number = "38",
pages = "131456",
doi = "10.1016/j.tet.2020.131456"
}
Milovanović, V. M., Petrović, Z. D., Novaković, S. B., Bogdanović, G. A., Petrović, V. P.,& Simijonović, D.. (2020). Green synthesis of benzamide-dioxoisoindoline derivatives and assessment of their radical scavenging activity – Experimental and theoretical approach. in Tetrahedron, 76(38), 131456.
https://doi.org/10.1016/j.tet.2020.131456
Milovanović VM, Petrović ZD, Novaković SB, Bogdanović GA, Petrović VP, Simijonović D. Green synthesis of benzamide-dioxoisoindoline derivatives and assessment of their radical scavenging activity – Experimental and theoretical approach. in Tetrahedron. 2020;76(38):131456.
doi:10.1016/j.tet.2020.131456 .
Milovanović, Vesna M, Petrović, Zorica D., Novaković, Slađana B., Bogdanović, Goran A., Petrović, Vladimir P., Simijonović, Dušica, "Green synthesis of benzamide-dioxoisoindoline derivatives and assessment of their radical scavenging activity – Experimental and theoretical approach" in Tetrahedron, 76, no. 38 (2020):131456,
https://doi.org/10.1016/j.tet.2020.131456 . .
7
1
5

Synthesis of new seven membered heterocyclic rings: An easy access to indeno-benzo[1,4]diazepines

Alam, Mohd Gulfam; Trifunović, Srećko R.; Bogdanović, Goran A.; Malla, Ali Mohammed; Mehdi, Sayed Hasan; Ghalib, Raza Murad

(2020)

TY  - JOUR
AU  - Alam, Mohd Gulfam
AU  - Trifunović, Srećko R.
AU  - Bogdanović, Goran A.
AU  - Malla, Ali Mohammed
AU  - Mehdi, Sayed Hasan
AU  - Ghalib, Raza Murad
PY  - 2020
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/9635
AB  - An easy access has been demonstrated for seven membered diazepines and a six membered quinoxaline. The reaction proceeds rapidly with low-cost and readily available chemicals at mild temperature and provides straight forward access to diazepines and quinoxaline. All final products are new and confirmed by spectral analysis and by single crystal X-ray analysis. Two crystal structures of the diazepines have very similar compositions, exhibit similar conformations where four condensed and coplanar rings are placed in the same orientation to the rest of molecule.
T2  - Arabian Journal of Chemistry
T1  - Synthesis of new seven membered heterocyclic rings: An easy access to indeno-benzo[1,4]diazepines
VL  - 13
IS  - 10
SP  - 7338
EP  - 7345
DO  - 10.1016/j.arabjc.2020.08.011
ER  - 
@article{
author = "Alam, Mohd Gulfam and Trifunović, Srećko R. and Bogdanović, Goran A. and Malla, Ali Mohammed and Mehdi, Sayed Hasan and Ghalib, Raza Murad",
year = "2020",
abstract = "An easy access has been demonstrated for seven membered diazepines and a six membered quinoxaline. The reaction proceeds rapidly with low-cost and readily available chemicals at mild temperature and provides straight forward access to diazepines and quinoxaline. All final products are new and confirmed by spectral analysis and by single crystal X-ray analysis. Two crystal structures of the diazepines have very similar compositions, exhibit similar conformations where four condensed and coplanar rings are placed in the same orientation to the rest of molecule.",
journal = "Arabian Journal of Chemistry",
title = "Synthesis of new seven membered heterocyclic rings: An easy access to indeno-benzo[1,4]diazepines",
volume = "13",
number = "10",
pages = "7338-7345",
doi = "10.1016/j.arabjc.2020.08.011"
}
Alam, M. G., Trifunović, S. R., Bogdanović, G. A., Malla, A. M., Mehdi, S. H.,& Ghalib, R. M.. (2020). Synthesis of new seven membered heterocyclic rings: An easy access to indeno-benzo[1,4]diazepines. in Arabian Journal of Chemistry, 13(10), 7338-7345.
https://doi.org/10.1016/j.arabjc.2020.08.011
Alam MG, Trifunović SR, Bogdanović GA, Malla AM, Mehdi SH, Ghalib RM. Synthesis of new seven membered heterocyclic rings: An easy access to indeno-benzo[1,4]diazepines. in Arabian Journal of Chemistry. 2020;13(10):7338-7345.
doi:10.1016/j.arabjc.2020.08.011 .
Alam, Mohd Gulfam, Trifunović, Srećko R., Bogdanović, Goran A., Malla, Ali Mohammed, Mehdi, Sayed Hasan, Ghalib, Raza Murad, "Synthesis of new seven membered heterocyclic rings: An easy access to indeno-benzo[1,4]diazepines" in Arabian Journal of Chemistry, 13, no. 10 (2020):7338-7345,
https://doi.org/10.1016/j.arabjc.2020.08.011 . .
4
1
5

Discovery of the Biginelli hybrids as novel caspase-9 activators in apoptotic machines: Lipophilicity, molecular docking study, influence on angiogenesis gene and miR-21 expression levels

Janković, Nenad Ž.; Trifunović Ristovski, Jovana; Vraneš, Milan; Tot, Aleksandar; Petronijević, Jelena; Joksimović, Nenad; Stanojković, Tatjana P.; Đorđić Crnogorac, Marija; Petrović, Nina; Boljević, Ivana; Matić, Ivana Z.; Bogdanović, Goran A.; Mikov, Momir; Bugarčić, Zorica M.

(2019)

TY  - JOUR
AU  - Janković, Nenad Ž.
AU  - Trifunović Ristovski, Jovana
AU  - Vraneš, Milan
AU  - Tot, Aleksandar
AU  - Petronijević, Jelena
AU  - Joksimović, Nenad
AU  - Stanojković, Tatjana P.
AU  - Đorđić Crnogorac, Marija
AU  - Petrović, Nina
AU  - Boljević, Ivana
AU  - Matić, Ivana Z.
AU  - Bogdanović, Goran A.
AU  - Mikov, Momir
AU  - Bugarčić, Zorica M.
PY  - 2019
UR  - https://linkinghub.elsevier.com/retrieve/pii/S0045206818312598
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8071
AB  - In order to investigate potential therapeutically agents, novel products of Biginelli reaction (4a-l) were synthesized and exposed to cytotoxic and caspase activities, angiogenesis, cell cycle distribution, gene and microRNA expression levels, lipophilicity assessment and docking study. Among the twelve novel compounds (4a-l) evaluated for the cytotoxic activity, five of them (4c, 4d, 4f, 4k and 4l) that showed excellent activity on the tested cell lines (HeLa, LS174 and A549) were selected for further evaluation. Interestingly, compound 4f has up to three times higher selectivity index (SI) towards cancer cells than cisplatin (on HeLa, LS174 and A549 SI = 18.2, 13.5 and 11.2, respectively). The obtained results from cell cycle distribution and caspase activity indicate that tested compounds (4c, 4d, 4f, 4k and 4l) promoted caspase-9 activation, implicated in the intrinsic pathway of apoptosis. Lipophilicity of 4a-l was determinate by using reversed-phase high-performance liquid chromatography. © 2019 Elsevier Inc.
T2  - Bioorganic Chemistry
T1  - Discovery of the Biginelli hybrids as novel caspase-9 activators in apoptotic machines: Lipophilicity, molecular docking study, influence on angiogenesis gene and miR-21 expression levels
VL  - 86
SP  - 569
EP  - 582
DO  - 10.1016/j.bioorg.2019.02.026
ER  - 
@article{
author = "Janković, Nenad Ž. and Trifunović Ristovski, Jovana and Vraneš, Milan and Tot, Aleksandar and Petronijević, Jelena and Joksimović, Nenad and Stanojković, Tatjana P. and Đorđić Crnogorac, Marija and Petrović, Nina and Boljević, Ivana and Matić, Ivana Z. and Bogdanović, Goran A. and Mikov, Momir and Bugarčić, Zorica M.",
year = "2019",
abstract = "In order to investigate potential therapeutically agents, novel products of Biginelli reaction (4a-l) were synthesized and exposed to cytotoxic and caspase activities, angiogenesis, cell cycle distribution, gene and microRNA expression levels, lipophilicity assessment and docking study. Among the twelve novel compounds (4a-l) evaluated for the cytotoxic activity, five of them (4c, 4d, 4f, 4k and 4l) that showed excellent activity on the tested cell lines (HeLa, LS174 and A549) were selected for further evaluation. Interestingly, compound 4f has up to three times higher selectivity index (SI) towards cancer cells than cisplatin (on HeLa, LS174 and A549 SI = 18.2, 13.5 and 11.2, respectively). The obtained results from cell cycle distribution and caspase activity indicate that tested compounds (4c, 4d, 4f, 4k and 4l) promoted caspase-9 activation, implicated in the intrinsic pathway of apoptosis. Lipophilicity of 4a-l was determinate by using reversed-phase high-performance liquid chromatography. © 2019 Elsevier Inc.",
journal = "Bioorganic Chemistry",
title = "Discovery of the Biginelli hybrids as novel caspase-9 activators in apoptotic machines: Lipophilicity, molecular docking study, influence on angiogenesis gene and miR-21 expression levels",
volume = "86",
pages = "569-582",
doi = "10.1016/j.bioorg.2019.02.026"
}
Janković, N. Ž., Trifunović Ristovski, J., Vraneš, M., Tot, A., Petronijević, J., Joksimović, N., Stanojković, T. P., Đorđić Crnogorac, M., Petrović, N., Boljević, I., Matić, I. Z., Bogdanović, G. A., Mikov, M.,& Bugarčić, Z. M.. (2019). Discovery of the Biginelli hybrids as novel caspase-9 activators in apoptotic machines: Lipophilicity, molecular docking study, influence on angiogenesis gene and miR-21 expression levels. in Bioorganic Chemistry, 86, 569-582.
https://doi.org/10.1016/j.bioorg.2019.02.026
Janković NŽ, Trifunović Ristovski J, Vraneš M, Tot A, Petronijević J, Joksimović N, Stanojković TP, Đorđić Crnogorac M, Petrović N, Boljević I, Matić IZ, Bogdanović GA, Mikov M, Bugarčić ZM. Discovery of the Biginelli hybrids as novel caspase-9 activators in apoptotic machines: Lipophilicity, molecular docking study, influence on angiogenesis gene and miR-21 expression levels. in Bioorganic Chemistry. 2019;86:569-582.
doi:10.1016/j.bioorg.2019.02.026 .
Janković, Nenad Ž., Trifunović Ristovski, Jovana, Vraneš, Milan, Tot, Aleksandar, Petronijević, Jelena, Joksimović, Nenad, Stanojković, Tatjana P., Đorđić Crnogorac, Marija, Petrović, Nina, Boljević, Ivana, Matić, Ivana Z., Bogdanović, Goran A., Mikov, Momir, Bugarčić, Zorica M., "Discovery of the Biginelli hybrids as novel caspase-9 activators in apoptotic machines: Lipophilicity, molecular docking study, influence on angiogenesis gene and miR-21 expression levels" in Bioorganic Chemistry, 86 (2019):569-582,
https://doi.org/10.1016/j.bioorg.2019.02.026 . .
17
6
17

Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study

Joksimović, Nenad; Petronijević, Jelena; Janković, Nenad Ž.; Baskić, Dejan; Popović, Suzana Lj.; Todorović, Danijela V.; Matić, Sanja Lj.; Bogdanović, Goran A.; Vraneš, Milan; Tot, Aleksandar; Bugarčić, Zorica M.

(2019)

TY  - JOUR
AU  - Joksimović, Nenad
AU  - Petronijević, Jelena
AU  - Janković, Nenad Ž.
AU  - Baskić, Dejan
AU  - Popović, Suzana Lj.
AU  - Todorović, Danijela V.
AU  - Matić, Sanja Lj.
AU  - Bogdanović, Goran A.
AU  - Vraneš, Milan
AU  - Tot, Aleksandar
AU  - Bugarčić, Zorica M.
PY  - 2019
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8173
AB  - In order to make a progress in discovering a new agents for chemotherapy with improved properties and bearing in mind the fact that substituted 3-hydroxy-3-pyrrolin-2-ones belong to a class of biologically active compounds, series of novel 1,5-diaryl-4-(2-thienylcarbonyl)-3-hydroxy-3-pyrrolin-2-ones were synthesized and characterized by spectral (UV–Vis, IR, NMR, ESI-MS), X-ray and elemental analysis. All compounds were examined for their cytotoxic effect on human cancer cell lines HeLa and MDA-MB 231 and normal fibroblasts (MRC-5). Four compounds, 3-hydroxy-1-(p-tolyl)-4-(2-thienylcarbonyl)-5-(4-chlorophenyl)-2,5-dihydro-1H-pyrrol-2-one (D10), 3-hydroxy-1-(3-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D13), 3-hydroxy-1-(4-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D14), and 3-hydroxy-1-(4-chlorophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D15), that showed the highest cytotoxicity against malignant cells and the best selectivity towards normal cells were selected for further experiments. Results obtained by investigating mechanisms of cytotoxic activity suggest that selected 3-hydroxy-3-pyrrolin-2-one derivatives in HeLa cells induce apoptosis that is associated with S phase arrest (D13, D15, and D10) or unrelated to cell cycle distribution (D14). Additionally, to better understand their suitability for potential use as anticancer medicaments we studied the interactions between biomacromolecules (DNA or BSA) and D13 and D15. The results indicated that D13 and D15 have great affinity to displace EB from the EB-DNA complex through intercalation [K sv = (3.7 ± 0.1) and (3.4 ± 0.1) × 10 3 M −1 , respectively], an intercalative mode also confirmed through viscosity measurements. K a values, obtained as result of fluorescence titration of BSA with D13 and D15 [K a = (4.2 ± 0.2) and (2.6 ± 0.2) × 10 5 M, respectively], support the fact that a significant amount of the tested compounds could be transported and distributed through the cells. In addition, by DNA and BSA molecular docking study for D13, D14 and D15 is determined and predicted the binding mode and the interaction region. © 2019 Elsevier Inc.
T2  - Bioorganic Chemistry
T1  - Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study
VL  - 88
SP  - 102954
DO  - 10.1016/j.bioorg.2019.102954
ER  - 
@article{
author = "Joksimović, Nenad and Petronijević, Jelena and Janković, Nenad Ž. and Baskić, Dejan and Popović, Suzana Lj. and Todorović, Danijela V. and Matić, Sanja Lj. and Bogdanović, Goran A. and Vraneš, Milan and Tot, Aleksandar and Bugarčić, Zorica M.",
year = "2019",
abstract = "In order to make a progress in discovering a new agents for chemotherapy with improved properties and bearing in mind the fact that substituted 3-hydroxy-3-pyrrolin-2-ones belong to a class of biologically active compounds, series of novel 1,5-diaryl-4-(2-thienylcarbonyl)-3-hydroxy-3-pyrrolin-2-ones were synthesized and characterized by spectral (UV–Vis, IR, NMR, ESI-MS), X-ray and elemental analysis. All compounds were examined for their cytotoxic effect on human cancer cell lines HeLa and MDA-MB 231 and normal fibroblasts (MRC-5). Four compounds, 3-hydroxy-1-(p-tolyl)-4-(2-thienylcarbonyl)-5-(4-chlorophenyl)-2,5-dihydro-1H-pyrrol-2-one (D10), 3-hydroxy-1-(3-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D13), 3-hydroxy-1-(4-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D14), and 3-hydroxy-1-(4-chlorophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D15), that showed the highest cytotoxicity against malignant cells and the best selectivity towards normal cells were selected for further experiments. Results obtained by investigating mechanisms of cytotoxic activity suggest that selected 3-hydroxy-3-pyrrolin-2-one derivatives in HeLa cells induce apoptosis that is associated with S phase arrest (D13, D15, and D10) or unrelated to cell cycle distribution (D14). Additionally, to better understand their suitability for potential use as anticancer medicaments we studied the interactions between biomacromolecules (DNA or BSA) and D13 and D15. The results indicated that D13 and D15 have great affinity to displace EB from the EB-DNA complex through intercalation [K sv = (3.7 ± 0.1) and (3.4 ± 0.1) × 10 3 M −1 , respectively], an intercalative mode also confirmed through viscosity measurements. K a values, obtained as result of fluorescence titration of BSA with D13 and D15 [K a = (4.2 ± 0.2) and (2.6 ± 0.2) × 10 5 M, respectively], support the fact that a significant amount of the tested compounds could be transported and distributed through the cells. In addition, by DNA and BSA molecular docking study for D13, D14 and D15 is determined and predicted the binding mode and the interaction region. © 2019 Elsevier Inc.",
journal = "Bioorganic Chemistry",
title = "Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study",
volume = "88",
pages = "102954",
doi = "10.1016/j.bioorg.2019.102954"
}
Joksimović, N., Petronijević, J., Janković, N. Ž., Baskić, D., Popović, S. Lj., Todorović, D. V., Matić, S. Lj., Bogdanović, G. A., Vraneš, M., Tot, A.,& Bugarčić, Z. M.. (2019). Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study. in Bioorganic Chemistry, 88, 102954.
https://doi.org/10.1016/j.bioorg.2019.102954
Joksimović N, Petronijević J, Janković NŽ, Baskić D, Popović SL, Todorović DV, Matić SL, Bogdanović GA, Vraneš M, Tot A, Bugarčić ZM. Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study. in Bioorganic Chemistry. 2019;88:102954.
doi:10.1016/j.bioorg.2019.102954 .
Joksimović, Nenad, Petronijević, Jelena, Janković, Nenad Ž., Baskić, Dejan, Popović, Suzana Lj., Todorović, Danijela V., Matić, Sanja Lj., Bogdanović, Goran A., Vraneš, Milan, Tot, Aleksandar, Bugarčić, Zorica M., "Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study" in Bioorganic Chemistry, 88 (2019):102954,
https://doi.org/10.1016/j.bioorg.2019.102954 . .
1
21
9
20

Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study

Joksimović, Nenad; Petronijević, Jelena; Janković, Nenad Ž.; Baskić, Dejan; Popović, Suzana Lj.; Todorović, Danijela V.; Matić, Sanja Lj.; Bogdanović, Goran A.; Vraneš, Milan; Tot, Aleksandar; Bugarčić, Zorica M.

(2019)

TY  - JOUR
AU  - Joksimović, Nenad
AU  - Petronijević, Jelena
AU  - Janković, Nenad Ž.
AU  - Baskić, Dejan
AU  - Popović, Suzana Lj.
AU  - Todorović, Danijela V.
AU  - Matić, Sanja Lj.
AU  - Bogdanović, Goran A.
AU  - Vraneš, Milan
AU  - Tot, Aleksandar
AU  - Bugarčić, Zorica M.
PY  - 2019
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8186
AB  - In order to make a progress in discovering a new agents for chemotherapy with improved properties and bearing in mind the fact that substituted 3-hydroxy-3-pyrrolin-2-ones belong to a class of biologically active compounds, series of novel 1,5-diaryl-4-(2-thienylcarbonyl)-3-hydroxy-3-pyrrolin-2-ones were synthesized and characterized by spectral (UV–Vis, IR, NMR, ESI-MS), X-ray and elemental analysis. All compounds were examined for their cytotoxic effect on human cancer cell lines HeLa and MDA-MB 231 and normal fibroblasts (MRC-5). Four compounds, 3-hydroxy-1-(p-tolyl)-4-(2-thienylcarbonyl)-5-(4-chlorophenyl)-2,5-dihydro-1H-pyrrol-2-one (D10), 3-hydroxy-1-(3-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D13), 3-hydroxy-1-(4-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D14), and 3-hydroxy-1-(4-chlorophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D15), that showed the highest cytotoxicity against malignant cells and the best selectivity towards normal cells were selected for further experiments. Results obtained by investigating mechanisms of cytotoxic activity suggest that selected 3-hydroxy-3-pyrrolin-2-one derivatives in HeLa cells induce apoptosis that is associated with S phase arrest (D13, D15, and D10) or unrelated to cell cycle distribution (D14). Additionally, to better understand their suitability for potential use as anticancer medicaments we studied the interactions between biomacromolecules (DNA or BSA) and D13 and D15. The results indicated that D13 and D15 have great affinity to displace EB from the EB-DNA complex through intercalation [K sv = (3.7 ± 0.1) and (3.4 ± 0.1) × 10 3 M −1 , respectively], an intercalative mode also confirmed through viscosity measurements. K a values, obtained as result of fluorescence titration of BSA with D13 and D15 [K a = (4.2 ± 0.2) and (2.6 ± 0.2) × 10 5 M, respectively], support the fact that a significant amount of the tested compounds could be transported and distributed through the cells. In addition, by DNA and BSA molecular docking study for D13, D14 and D15 is determined and predicted the binding mode and the interaction region. © 2019 Elsevier Inc.
T2  - Bioorganic Chemistry
T1  - Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study
VL  - 88
SP  - 102954
DO  - 10.1016/j.bioorg.2019.102954
ER  - 
@article{
author = "Joksimović, Nenad and Petronijević, Jelena and Janković, Nenad Ž. and Baskić, Dejan and Popović, Suzana Lj. and Todorović, Danijela V. and Matić, Sanja Lj. and Bogdanović, Goran A. and Vraneš, Milan and Tot, Aleksandar and Bugarčić, Zorica M.",
year = "2019",
abstract = "In order to make a progress in discovering a new agents for chemotherapy with improved properties and bearing in mind the fact that substituted 3-hydroxy-3-pyrrolin-2-ones belong to a class of biologically active compounds, series of novel 1,5-diaryl-4-(2-thienylcarbonyl)-3-hydroxy-3-pyrrolin-2-ones were synthesized and characterized by spectral (UV–Vis, IR, NMR, ESI-MS), X-ray and elemental analysis. All compounds were examined for their cytotoxic effect on human cancer cell lines HeLa and MDA-MB 231 and normal fibroblasts (MRC-5). Four compounds, 3-hydroxy-1-(p-tolyl)-4-(2-thienylcarbonyl)-5-(4-chlorophenyl)-2,5-dihydro-1H-pyrrol-2-one (D10), 3-hydroxy-1-(3-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D13), 3-hydroxy-1-(4-nitrophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D14), and 3-hydroxy-1-(4-chlorophenyl)-4-(2-thienylcarbonyl)-5-(4-(benzyloxy)phenyl)-2,5-dihydro-1H-pyrrol-2-one (D15), that showed the highest cytotoxicity against malignant cells and the best selectivity towards normal cells were selected for further experiments. Results obtained by investigating mechanisms of cytotoxic activity suggest that selected 3-hydroxy-3-pyrrolin-2-one derivatives in HeLa cells induce apoptosis that is associated with S phase arrest (D13, D15, and D10) or unrelated to cell cycle distribution (D14). Additionally, to better understand their suitability for potential use as anticancer medicaments we studied the interactions between biomacromolecules (DNA or BSA) and D13 and D15. The results indicated that D13 and D15 have great affinity to displace EB from the EB-DNA complex through intercalation [K sv = (3.7 ± 0.1) and (3.4 ± 0.1) × 10 3 M −1 , respectively], an intercalative mode also confirmed through viscosity measurements. K a values, obtained as result of fluorescence titration of BSA with D13 and D15 [K a = (4.2 ± 0.2) and (2.6 ± 0.2) × 10 5 M, respectively], support the fact that a significant amount of the tested compounds could be transported and distributed through the cells. In addition, by DNA and BSA molecular docking study for D13, D14 and D15 is determined and predicted the binding mode and the interaction region. © 2019 Elsevier Inc.",
journal = "Bioorganic Chemistry",
title = "Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study",
volume = "88",
pages = "102954",
doi = "10.1016/j.bioorg.2019.102954"
}
Joksimović, N., Petronijević, J., Janković, N. Ž., Baskić, D., Popović, S. Lj., Todorović, D. V., Matić, S. Lj., Bogdanović, G. A., Vraneš, M., Tot, A.,& Bugarčić, Z. M.. (2019). Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study. in Bioorganic Chemistry, 88, 102954.
https://doi.org/10.1016/j.bioorg.2019.102954
Joksimović N, Petronijević J, Janković NŽ, Baskić D, Popović SL, Todorović DV, Matić SL, Bogdanović GA, Vraneš M, Tot A, Bugarčić ZM. Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study. in Bioorganic Chemistry. 2019;88:102954.
doi:10.1016/j.bioorg.2019.102954 .
Joksimović, Nenad, Petronijević, Jelena, Janković, Nenad Ž., Baskić, Dejan, Popović, Suzana Lj., Todorović, Danijela V., Matić, Sanja Lj., Bogdanović, Goran A., Vraneš, Milan, Tot, Aleksandar, Bugarčić, Zorica M., "Synthesis, characterization, anticancer evaluation and mechanisms of cytotoxic activity of novel 3-hydroxy-3-pyrrolin-2-ones bearing thenoyl fragment: DNA, BSA interactions and molecular docking study" in Bioorganic Chemistry, 88 (2019):102954,
https://doi.org/10.1016/j.bioorg.2019.102954 . .
1
21
9
20

Interactions of binuclear copper(II) complexes with S-substituted thiosalicylate derivatives with some relevant biomolecules

Jovanović, Snežana; Bogojeski, Jovana V.; Nikolić, Miloš V.; Mijajlović, Marina Ž.; Tomović, Dušan Lj.; Bukonjić, Andriana M.; Knežević Rangelov, Sanja M.; Mijailović, Nataša R.; Ratković, Zoran R.; Jevtić, Verica V.; Petrović, Biljana V.; Trifunović, Srećko R.; Novaković, Slađana B.; Bogdanović, Goran A.; Radić, Gordana P.

(2019)

TY  - JOUR
AU  - Jovanović, Snežana
AU  - Bogojeski, Jovana V.
AU  - Nikolić, Miloš V.
AU  - Mijajlović, Marina Ž.
AU  - Tomović, Dušan Lj.
AU  - Bukonjić, Andriana M.
AU  - Knežević Rangelov, Sanja M.
AU  - Mijailović, Nataša R.
AU  - Ratković, Zoran R.
AU  - Jevtić, Verica V.
AU  - Petrović, Biljana V.
AU  - Trifunović, Srećko R.
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Radić, Gordana P.
PY  - 2019
UR  - https://www.tandfonline.com/doi/full/10.1080/00958972.2019.1610561
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8196
AB  - Interactions of copper(II) complexes which contain S-alkyl derivatives of thiosalicylic acid (alkyl = methyl, ethyl, propyl and butyl; aryl = benzyl), marked as 1–5, with guanosine-5′-monophosphate (5′-GMP) and calf thymus DNA (CT-DNA) were studied. Kinetics of substitution reactions of 1–5 with 5′-GMP and CT-DNA were investigated under pseudo-first-order conditions at 310 K and pH = 7.2 in 25 mM Hepes buffer using stopped-flow method. All complexes have high affinity toward studied bio-molecules. Additionally, interactions with CT-DNA were followed by absorption spectroscopy and fluorescence quenching measurements. The results indicate that complexes bind to DNA exhibiting high binding constants (Kb = 104 M−1). During the examination of competitive reactions with ethidium bromide (EB), results showed that complexes can replace EB-bound DNA. In addition, a new crystal structure of the binuclear Cu(II) complex with S-substituted thiosalicylate derivative has been reported. In the present series of Cu(II) complexes the crystal structure is the first example of a complex comprising an S-aryl derivative of thiosalicylate ligand. Through comparative study of structural properties of six molecules from four crystal structures we examined the structural variations, potentially important for biological activity of these complexes. © 2019, © 2019 Informa UK Limited, trading as Taylor & Francis Group.
T2  - Journal of Coordination Chemistry
T1  - Interactions of binuclear copper(II) complexes with S-substituted thiosalicylate derivatives with some relevant biomolecules
VL  - 72
IS  - 10
SP  - 1603
EP  - 1620
DO  - 10.1080/00958972.2019.1610561
ER  - 
@article{
author = "Jovanović, Snežana and Bogojeski, Jovana V. and Nikolić, Miloš V. and Mijajlović, Marina Ž. and Tomović, Dušan Lj. and Bukonjić, Andriana M. and Knežević Rangelov, Sanja M. and Mijailović, Nataša R. and Ratković, Zoran R. and Jevtić, Verica V. and Petrović, Biljana V. and Trifunović, Srećko R. and Novaković, Slađana B. and Bogdanović, Goran A. and Radić, Gordana P.",
year = "2019",
abstract = "Interactions of copper(II) complexes which contain S-alkyl derivatives of thiosalicylic acid (alkyl = methyl, ethyl, propyl and butyl; aryl = benzyl), marked as 1–5, with guanosine-5′-monophosphate (5′-GMP) and calf thymus DNA (CT-DNA) were studied. Kinetics of substitution reactions of 1–5 with 5′-GMP and CT-DNA were investigated under pseudo-first-order conditions at 310 K and pH = 7.2 in 25 mM Hepes buffer using stopped-flow method. All complexes have high affinity toward studied bio-molecules. Additionally, interactions with CT-DNA were followed by absorption spectroscopy and fluorescence quenching measurements. The results indicate that complexes bind to DNA exhibiting high binding constants (Kb = 104 M−1). During the examination of competitive reactions with ethidium bromide (EB), results showed that complexes can replace EB-bound DNA. In addition, a new crystal structure of the binuclear Cu(II) complex with S-substituted thiosalicylate derivative has been reported. In the present series of Cu(II) complexes the crystal structure is the first example of a complex comprising an S-aryl derivative of thiosalicylate ligand. Through comparative study of structural properties of six molecules from four crystal structures we examined the structural variations, potentially important for biological activity of these complexes. © 2019, © 2019 Informa UK Limited, trading as Taylor & Francis Group.",
journal = "Journal of Coordination Chemistry",
title = "Interactions of binuclear copper(II) complexes with S-substituted thiosalicylate derivatives with some relevant biomolecules",
volume = "72",
number = "10",
pages = "1603-1620",
doi = "10.1080/00958972.2019.1610561"
}
Jovanović, S., Bogojeski, J. V., Nikolić, M. V., Mijajlović, M. Ž., Tomović, D. Lj., Bukonjić, A. M., Knežević Rangelov, S. M., Mijailović, N. R., Ratković, Z. R., Jevtić, V. V., Petrović, B. V., Trifunović, S. R., Novaković, S. B., Bogdanović, G. A.,& Radić, G. P.. (2019). Interactions of binuclear copper(II) complexes with S-substituted thiosalicylate derivatives with some relevant biomolecules. in Journal of Coordination Chemistry, 72(10), 1603-1620.
https://doi.org/10.1080/00958972.2019.1610561
Jovanović S, Bogojeski JV, Nikolić MV, Mijajlović MŽ, Tomović DL, Bukonjić AM, Knežević Rangelov SM, Mijailović NR, Ratković ZR, Jevtić VV, Petrović BV, Trifunović SR, Novaković SB, Bogdanović GA, Radić GP. Interactions of binuclear copper(II) complexes with S-substituted thiosalicylate derivatives with some relevant biomolecules. in Journal of Coordination Chemistry. 2019;72(10):1603-1620.
doi:10.1080/00958972.2019.1610561 .
Jovanović, Snežana, Bogojeski, Jovana V., Nikolić, Miloš V., Mijajlović, Marina Ž., Tomović, Dušan Lj., Bukonjić, Andriana M., Knežević Rangelov, Sanja M., Mijailović, Nataša R., Ratković, Zoran R., Jevtić, Verica V., Petrović, Biljana V., Trifunović, Srećko R., Novaković, Slađana B., Bogdanović, Goran A., Radić, Gordana P., "Interactions of binuclear copper(II) complexes with S-substituted thiosalicylate derivatives with some relevant biomolecules" in Journal of Coordination Chemistry, 72, no. 10 (2019):1603-1620,
https://doi.org/10.1080/00958972.2019.1610561 . .
3
2

Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach

Milovanović, Vesna M.; Petrović, Zorica D.; Novaković, Slađana B.; Bogdanović, Goran A.; Simijonović, Dušica; Petrović, Vladimir P.

(2019)

TY  - JOUR
AU  - Milovanović, Vesna M.
AU  - Petrović, Zorica D.
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Simijonović, Dušica
AU  - Petrović, Vladimir P.
PY  - 2019
UR  - https://linkinghub.elsevier.com/retrieve/pii/S0022286019306659
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8224
AB  - Simple, one-pot, and low-cost reactions of acetylacetone with a variety of substituted benzoyl hydrazides in lemon juice, as eco-friendly medium, were performed. In reactions of benzoyl hydrazides with electron-donating groups on phenyl ring, the 1-benzoyl-1H-pyrazole derivatives were obtained in short reaction time, and in good to high yields. On the other hand, benzoyl hydrazides with electron-withdrawing groups reacted slower, yielding the mixture of 1-benzoyl-5-hydroxy-4,5-dihydro-1H-pyrazole and benzoyl-1H-pyrazole derivatives. It is worth pointing out that two products, (2-chlorophenyl)(4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)methanone and (4-iodophenyl)(3,5-dimethyl-1H-pyrazol-1-yl)methanone are reported here for the first time. All obtained compounds were characterized using IR, UV–Vis and NMR, experimentally and theoretically, as well as with melting points. Good agreement between experimental and simulated IR, UV–Vis, 1H and 13C NMR spectra was achieved. In addition, crystal structures and Hirshfeld surfaces analysis of (4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)(4-iodophenyl)methanone were reported. © 2019 Elsevier B.V.
T2  - Journal of Molecular Structure
T1  - Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach
VL  - 1195
SP  - 85
EP  - 94
DO  - 10.1016/j.molstruc.2019.05.095
ER  - 
@article{
author = "Milovanović, Vesna M. and Petrović, Zorica D. and Novaković, Slađana B. and Bogdanović, Goran A. and Simijonović, Dušica and Petrović, Vladimir P.",
year = "2019",
abstract = "Simple, one-pot, and low-cost reactions of acetylacetone with a variety of substituted benzoyl hydrazides in lemon juice, as eco-friendly medium, were performed. In reactions of benzoyl hydrazides with electron-donating groups on phenyl ring, the 1-benzoyl-1H-pyrazole derivatives were obtained in short reaction time, and in good to high yields. On the other hand, benzoyl hydrazides with electron-withdrawing groups reacted slower, yielding the mixture of 1-benzoyl-5-hydroxy-4,5-dihydro-1H-pyrazole and benzoyl-1H-pyrazole derivatives. It is worth pointing out that two products, (2-chlorophenyl)(4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)methanone and (4-iodophenyl)(3,5-dimethyl-1H-pyrazol-1-yl)methanone are reported here for the first time. All obtained compounds were characterized using IR, UV–Vis and NMR, experimentally and theoretically, as well as with melting points. Good agreement between experimental and simulated IR, UV–Vis, 1H and 13C NMR spectra was achieved. In addition, crystal structures and Hirshfeld surfaces analysis of (4,5-dihydro-5-hydroxy-3,5-dimethylpyrazol-1-yl)(4-iodophenyl)methanone were reported. © 2019 Elsevier B.V.",
journal = "Journal of Molecular Structure",
title = "Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach",
volume = "1195",
pages = "85-94",
doi = "10.1016/j.molstruc.2019.05.095"
}
Milovanović, V. M., Petrović, Z. D., Novaković, S. B., Bogdanović, G. A., Simijonović, D.,& Petrović, V. P.. (2019). Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach. in Journal of Molecular Structure, 1195, 85-94.
https://doi.org/10.1016/j.molstruc.2019.05.095
Milovanović VM, Petrović ZD, Novaković SB, Bogdanović GA, Simijonović D, Petrović VP. Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach. in Journal of Molecular Structure. 2019;1195:85-94.
doi:10.1016/j.molstruc.2019.05.095 .
Milovanović, Vesna M., Petrović, Zorica D., Novaković, Slađana B., Bogdanović, Goran A., Simijonović, Dušica, Petrović, Vladimir P., "Structural characterization of benzoyl-1H-pyrazole derivatives obtained in lemon juice medium: Experimental and theoretical approach" in Journal of Molecular Structure, 1195 (2019):85-94,
https://doi.org/10.1016/j.molstruc.2019.05.095 . .
8
5
8

Crystal structure of dihydrazinium 1H-pyrazole-3,5-dicarboxylate, C5H12N6O4

Latinović, Nedeljko; Novaković, Slađana B.; Bogdanović, Goran A.; Kastratović, Vlatko; Giester, Gerald; Jaćimović, Željko K.

(2019)

TY  - JOUR
AU  - Latinović, Nedeljko
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Kastratović, Vlatko
AU  - Giester, Gerald
AU  - Jaćimović, Željko K.
PY  - 2019
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8376
AB  - C 5 H 12 N 6 O 4 , monoclinic, P 2 1 / n (no. 14), a = 4.3368(6) Å, b = 15.483(2) Å, c = 13.8852(19) Å, β = 97.714(3)°, V = 923.9(2) Å 3 , Z = 4, R gt ( F ) = 0.0411, wR ref ( F 2 ) = 0.1109, T = 200(2) K.
T2  - Zeitschrift für Kristallographie - New Crystal Structures
T1  - Crystal structure of dihydrazinium 1H-pyrazole-3,5-dicarboxylate, C5H12N6O4
VL  - 234
IS  - 5
SP  - 957
EP  - 958
DO  - 10.1515/ncrs-2019-0168
ER  - 
@article{
author = "Latinović, Nedeljko and Novaković, Slađana B. and Bogdanović, Goran A. and Kastratović, Vlatko and Giester, Gerald and Jaćimović, Željko K.",
year = "2019",
abstract = "C 5 H 12 N 6 O 4 , monoclinic, P 2 1 / n (no. 14), a = 4.3368(6) Å, b = 15.483(2) Å, c = 13.8852(19) Å, β = 97.714(3)°, V = 923.9(2) Å 3 , Z = 4, R gt ( F ) = 0.0411, wR ref ( F 2 ) = 0.1109, T = 200(2) K.",
journal = "Zeitschrift für Kristallographie - New Crystal Structures",
title = "Crystal structure of dihydrazinium 1H-pyrazole-3,5-dicarboxylate, C5H12N6O4",
volume = "234",
number = "5",
pages = "957-958",
doi = "10.1515/ncrs-2019-0168"
}
Latinović, N., Novaković, S. B., Bogdanović, G. A., Kastratović, V., Giester, G.,& Jaćimović, Ž. K.. (2019). Crystal structure of dihydrazinium 1H-pyrazole-3,5-dicarboxylate, C5H12N6O4. in Zeitschrift für Kristallographie - New Crystal Structures, 234(5), 957-958.
https://doi.org/10.1515/ncrs-2019-0168
Latinović N, Novaković SB, Bogdanović GA, Kastratović V, Giester G, Jaćimović ŽK. Crystal structure of dihydrazinium 1H-pyrazole-3,5-dicarboxylate, C5H12N6O4. in Zeitschrift für Kristallographie - New Crystal Structures. 2019;234(5):957-958.
doi:10.1515/ncrs-2019-0168 .
Latinović, Nedeljko, Novaković, Slađana B., Bogdanović, Goran A., Kastratović, Vlatko, Giester, Gerald, Jaćimović, Željko K., "Crystal structure of dihydrazinium 1H-pyrazole-3,5-dicarboxylate, C5H12N6O4" in Zeitschrift für Kristallographie - New Crystal Structures, 234, no. 5 (2019):957-958,
https://doi.org/10.1515/ncrs-2019-0168 . .
2
1

First crystal structures of metal complexes with a 4-nitropyrazole-3-carboxylic acid ligand and the third crystal form of the ligand

Jaćimović, Željko K.; Novaković, Slađana B.; Bogdanović, Goran A.; Giester, Gerald; Kosović, Milica; Libowitzky, Eugen

(2019)

TY  - JOUR
AU  - Jaćimović, Željko K.
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Giester, Gerald
AU  - Kosović, Milica
AU  - Libowitzky, Eugen
PY  - 2019
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/8540
AB  - Pyrazole (pz)-derived ligands can, besides exhibiting a strong coordination ability toward different metal ions, exhibit a great diversity in their coordination geometry and nuclearity, which can be achieved by varying the type and position of the pz substituents. The present study reports the synthesis and crystal structure of two binuclear complexes, namely bis(μ-4-nitro-1 H -imidazol-1-ide-5-carboxylato)-κ 3 N 1 , O : N 2 ;κ 3 N 2 : N 1 , O -bis[aqua(dimethylformamide-κ O )copper(II)], [Cu 2 (C 4 HN 3 O 4 ) 2 (C 3 H 7 NO) 2 (H 2 O) 2 ], (II), and bis(μ-4-nitro-1 H -imidazol-1-ide-5-carboxylato)-κ 2 N 1 , O : N 2 ;κ 2 N 2 : N 1 , O -bis[triaquacobalt(II)] dihydrate, [Co 2 (C 4 HN 3 O 4 ) 2 (H 2 O) 6 ]·2H 2 O, (III). These compounds represent rare examples of metal complexes comprising 3,4-substituted pz derivatives as a bridging ligand and also the first crystal structures of transition-metal complexes with ligands derived from 4-nitropyrazole-3-carboxylic acid. Recently, the crystal structures of the same ligand in the neutral and mixed neutral/anionic forms have been reported. We present here the third form of this ligand, where it is present in a fully deprotonated anionic form within a salt, i.e. ammonium 4-nitropyrazole-3-carboxylate, NH 4 + ·C 4 H 2 N 3 O 4 − , (I). Single-crystal X-ray diffraction revealed that in the present complexes, the Cu II and Co II centres adopt distorted square-pyramidal and octahedral geometries, respectively. In both cases, the N , N ′, O -coordinated pz ligand shows simultaneously chelating and bridging coordination modes, leading to the formation of a nearly planar six-membered M 2 N 4 metallocycle. In all three crystal structures, the supramolecular arrangement is controlled by strong hydrogen bonds which primarily engage the carboxylate O atoms as acceptors, while the nitro group adopts the role of an acceptor only in structures with an increased number of donors, as is the case with Co II complex (III). The electrostatic potential, as a descriptor of reactivity, was also calculated in order to examine the changes in ligand electrostatic preferences upon coordination to metal ions.
T2  - Acta Crystallographica Section C: Structural Chemistry
T1  - First crystal structures of metal complexes with a 4-nitropyrazole-3-carboxylic acid ligand and the third crystal form of the ligand
VL  - 75
IS  - 3
SP  - 255
EP  - 264
DO  - 10.1107/S2053229619001244
ER  - 
@article{
author = "Jaćimović, Željko K. and Novaković, Slađana B. and Bogdanović, Goran A. and Giester, Gerald and Kosović, Milica and Libowitzky, Eugen",
year = "2019",
abstract = "Pyrazole (pz)-derived ligands can, besides exhibiting a strong coordination ability toward different metal ions, exhibit a great diversity in their coordination geometry and nuclearity, which can be achieved by varying the type and position of the pz substituents. The present study reports the synthesis and crystal structure of two binuclear complexes, namely bis(μ-4-nitro-1 H -imidazol-1-ide-5-carboxylato)-κ 3 N 1 , O : N 2 ;κ 3 N 2 : N 1 , O -bis[aqua(dimethylformamide-κ O )copper(II)], [Cu 2 (C 4 HN 3 O 4 ) 2 (C 3 H 7 NO) 2 (H 2 O) 2 ], (II), and bis(μ-4-nitro-1 H -imidazol-1-ide-5-carboxylato)-κ 2 N 1 , O : N 2 ;κ 2 N 2 : N 1 , O -bis[triaquacobalt(II)] dihydrate, [Co 2 (C 4 HN 3 O 4 ) 2 (H 2 O) 6 ]·2H 2 O, (III). These compounds represent rare examples of metal complexes comprising 3,4-substituted pz derivatives as a bridging ligand and also the first crystal structures of transition-metal complexes with ligands derived from 4-nitropyrazole-3-carboxylic acid. Recently, the crystal structures of the same ligand in the neutral and mixed neutral/anionic forms have been reported. We present here the third form of this ligand, where it is present in a fully deprotonated anionic form within a salt, i.e. ammonium 4-nitropyrazole-3-carboxylate, NH 4 + ·C 4 H 2 N 3 O 4 − , (I). Single-crystal X-ray diffraction revealed that in the present complexes, the Cu II and Co II centres adopt distorted square-pyramidal and octahedral geometries, respectively. In both cases, the N , N ′, O -coordinated pz ligand shows simultaneously chelating and bridging coordination modes, leading to the formation of a nearly planar six-membered M 2 N 4 metallocycle. In all three crystal structures, the supramolecular arrangement is controlled by strong hydrogen bonds which primarily engage the carboxylate O atoms as acceptors, while the nitro group adopts the role of an acceptor only in structures with an increased number of donors, as is the case with Co II complex (III). The electrostatic potential, as a descriptor of reactivity, was also calculated in order to examine the changes in ligand electrostatic preferences upon coordination to metal ions.",
journal = "Acta Crystallographica Section C: Structural Chemistry",
title = "First crystal structures of metal complexes with a 4-nitropyrazole-3-carboxylic acid ligand and the third crystal form of the ligand",
volume = "75",
number = "3",
pages = "255-264",
doi = "10.1107/S2053229619001244"
}
Jaćimović, Ž. K., Novaković, S. B., Bogdanović, G. A., Giester, G., Kosović, M.,& Libowitzky, E.. (2019). First crystal structures of metal complexes with a 4-nitropyrazole-3-carboxylic acid ligand and the third crystal form of the ligand. in Acta Crystallographica Section C: Structural Chemistry, 75(3), 255-264.
https://doi.org/10.1107/S2053229619001244
Jaćimović ŽK, Novaković SB, Bogdanović GA, Giester G, Kosović M, Libowitzky E. First crystal structures of metal complexes with a 4-nitropyrazole-3-carboxylic acid ligand and the third crystal form of the ligand. in Acta Crystallographica Section C: Structural Chemistry. 2019;75(3):255-264.
doi:10.1107/S2053229619001244 .
Jaćimović, Željko K., Novaković, Slađana B., Bogdanović, Goran A., Giester, Gerald, Kosović, Milica, Libowitzky, Eugen, "First crystal structures of metal complexes with a 4-nitropyrazole-3-carboxylic acid ligand and the third crystal form of the ligand" in Acta Crystallographica Section C: Structural Chemistry, 75, no. 3 (2019):255-264,
https://doi.org/10.1107/S2053229619001244 . .
1
2
3
3

Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties

Burmudžija, Adrijana; Muškinja, Jovana; Ratković, Zoran R.; Kosanić, Marijana; Ranković, Branislav; Novaković, Slađana B.; Bogdanović, Goran A.

(2018)

TY  - JOUR
AU  - Burmudžija, Adrijana
AU  - Muškinja, Jovana
AU  - Ratković, Zoran R.
AU  - Kosanić, Marijana
AU  - Ranković, Branislav
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
PY  - 2018
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1910
AB  - A series of ferrocenyl ketones were synthesized in reaction with ferrocene and corresponding substituted acryloyl chlorides, following previously described procedure. Synthesized products have conjugated enone system, which is suitable for further transformations. In a reaction with hydrazine in acidic medium (acetic acid) new pyrazoline derivatives were obtained. Their antimicrobial properties have been tested. Synthesized pyrazoline derivatives demonstrated expressed in vitro antimicrobial activity towards 12 strains of microorganisms inhibiting all tested bacteria and fungi. The most potent compound in all cases was sorbyl derivative; for bacteria activity was very close to streptomycin, and for fungi in one case the same as ketoconazole. It is established that this compound can be a new, potential antimicrobial agent with minimum inhibitory concentrations from 0.039 to 0.312 mg/mL. One of the starting compounds and two products were crystal substances, suitable for the single crystal X-ray diffraction analysis, which confirmed undoubtedly their structures. (C) 2017 Elsevier B.V. All rights reserved.
T2  - Inorganica Chimica Acta
T1  - Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties
VL  - 471
SP  - 570
EP  - 576
DO  - 10.1016/j.ica.2017.11.061
ER  - 
@article{
author = "Burmudžija, Adrijana and Muškinja, Jovana and Ratković, Zoran R. and Kosanić, Marijana and Ranković, Branislav and Novaković, Slađana B. and Bogdanović, Goran A.",
year = "2018",
abstract = "A series of ferrocenyl ketones were synthesized in reaction with ferrocene and corresponding substituted acryloyl chlorides, following previously described procedure. Synthesized products have conjugated enone system, which is suitable for further transformations. In a reaction with hydrazine in acidic medium (acetic acid) new pyrazoline derivatives were obtained. Their antimicrobial properties have been tested. Synthesized pyrazoline derivatives demonstrated expressed in vitro antimicrobial activity towards 12 strains of microorganisms inhibiting all tested bacteria and fungi. The most potent compound in all cases was sorbyl derivative; for bacteria activity was very close to streptomycin, and for fungi in one case the same as ketoconazole. It is established that this compound can be a new, potential antimicrobial agent with minimum inhibitory concentrations from 0.039 to 0.312 mg/mL. One of the starting compounds and two products were crystal substances, suitable for the single crystal X-ray diffraction analysis, which confirmed undoubtedly their structures. (C) 2017 Elsevier B.V. All rights reserved.",
journal = "Inorganica Chimica Acta",
title = "Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties",
volume = "471",
pages = "570-576",
doi = "10.1016/j.ica.2017.11.061"
}
Burmudžija, A., Muškinja, J., Ratković, Z. R., Kosanić, M., Ranković, B., Novaković, S. B.,& Bogdanović, G. A.. (2018). Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties. in Inorganica Chimica Acta, 471, 570-576.
https://doi.org/10.1016/j.ica.2017.11.061
Burmudžija A, Muškinja J, Ratković ZR, Kosanić M, Ranković B, Novaković SB, Bogdanović GA. Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties. in Inorganica Chimica Acta. 2018;471:570-576.
doi:10.1016/j.ica.2017.11.061 .
Burmudžija, Adrijana, Muškinja, Jovana, Ratković, Zoran R., Kosanić, Marijana, Ranković, Branislav, Novaković, Slađana B., Bogdanović, Goran A., "Pyrazoline derivatives of acryloyl substituted ferrocenyl ketones: Synthesis, antimicrobial activity and structural properties" in Inorganica Chimica Acta, 471 (2018):570-576,
https://doi.org/10.1016/j.ica.2017.11.061 . .
9
8
10

Supporting information for: Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry

Janković, Nenad Ž.; Stefanović, Srđan M.; Petronijević, Jelena; Joksimović, Nenad; Novaković, Slađana B.; Bogdanović, Goran A.; Muškinja, Jovana; Vraneš, Milan; Ratković, Zoran R.; Bugarčić, Zorica M.

(2018)

TY  - DATA
AU  - Janković, Nenad Ž.
AU  - Stefanović, Srđan M.
AU  - Petronijević, Jelena
AU  - Joksimović, Nenad
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Muškinja, Jovana
AU  - Vraneš, Milan
AU  - Ratković, Zoran R.
AU  - Bugarčić, Zorica M.
PY  - 2018
UR  - http://pubs.acs.org/doi/10.1021/acssuschemeng.8b03127
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7886
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7888
AB  - The selective synthesis of 5,6-dihydropyrimidin-4(3H)-one scaffold (precursor of dihydrouracil) was a very difficult synthetic challenge that, so far, has not been achieved. For the first time, in this paper, green, selective and high-yields approach to 40 novel 5,6-dihydropyrimidin-4(3H)-ones (DHPMs) by one-pot reaction of aldehydes, Meldrum's acid and isothioureas under solvent-free conditions, in the presence of water, since an additive is presented. In the majority of cases, introduced methodology gave an unprecedented tautomer-selective fashion toward targeted compounds with excellent tautomeric purity (>99.9%), which reached 100% in few cases. The molecular structure of the five compounds has been determined by X-ray crystallography. In each one of them, very short length for the corresponding N2-C1 bond was noticed, making them especially interesting from a structural standpoint. This experimental fact can imply a highly localized electron π density in this part of each heterocyclic ring. The obtained experimental results, which are determined from NMR and ESI-MS study, indicate that this Biginelli-type reaction smoothly proceeds in a one-pot mode, pointing to the three-step tandem process, proceeding via the Knoevenagel, aza-Michael, and retro-Diels-Alder reactions. The presented strategy also had the following advantages: reduction amount of waste, excellent values of green chemistry metrics (cEF, EcoScale and GCIS), and it is the first eco-friendly strategy toward the DHPMs scaffold. © Copyright 2018 American Chemical Society.
T2  - ACS Sustainable Chemistry and Engineering
T1  - Supporting information for: Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry
VL  - 6
IS  - 10
SP  - 13358
EP  - 13366
DO  - 10.1021/acssuschemeng.8b03127.s006
ER  - 
@misc{
author = "Janković, Nenad Ž. and Stefanović, Srđan M. and Petronijević, Jelena and Joksimović, Nenad and Novaković, Slađana B. and Bogdanović, Goran A. and Muškinja, Jovana and Vraneš, Milan and Ratković, Zoran R. and Bugarčić, Zorica M.",
year = "2018",
abstract = "The selective synthesis of 5,6-dihydropyrimidin-4(3H)-one scaffold (precursor of dihydrouracil) was a very difficult synthetic challenge that, so far, has not been achieved. For the first time, in this paper, green, selective and high-yields approach to 40 novel 5,6-dihydropyrimidin-4(3H)-ones (DHPMs) by one-pot reaction of aldehydes, Meldrum's acid and isothioureas under solvent-free conditions, in the presence of water, since an additive is presented. In the majority of cases, introduced methodology gave an unprecedented tautomer-selective fashion toward targeted compounds with excellent tautomeric purity (>99.9%), which reached 100% in few cases. The molecular structure of the five compounds has been determined by X-ray crystallography. In each one of them, very short length for the corresponding N2-C1 bond was noticed, making them especially interesting from a structural standpoint. This experimental fact can imply a highly localized electron π density in this part of each heterocyclic ring. The obtained experimental results, which are determined from NMR and ESI-MS study, indicate that this Biginelli-type reaction smoothly proceeds in a one-pot mode, pointing to the three-step tandem process, proceeding via the Knoevenagel, aza-Michael, and retro-Diels-Alder reactions. The presented strategy also had the following advantages: reduction amount of waste, excellent values of green chemistry metrics (cEF, EcoScale and GCIS), and it is the first eco-friendly strategy toward the DHPMs scaffold. © Copyright 2018 American Chemical Society.",
journal = "ACS Sustainable Chemistry and Engineering",
title = "Supporting information for: Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry",
volume = "6",
number = "10",
pages = "13358-13366",
doi = "10.1021/acssuschemeng.8b03127.s006"
}
Janković, N. Ž., Stefanović, S. M., Petronijević, J., Joksimović, N., Novaković, S. B., Bogdanović, G. A., Muškinja, J., Vraneš, M., Ratković, Z. R.,& Bugarčić, Z. M.. (2018). Supporting information for: Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry. in ACS Sustainable Chemistry and Engineering, 6(10), 13358-13366.
https://doi.org/10.1021/acssuschemeng.8b03127.s006
Janković NŽ, Stefanović SM, Petronijević J, Joksimović N, Novaković SB, Bogdanović GA, Muškinja J, Vraneš M, Ratković ZR, Bugarčić ZM. Supporting information for: Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry. in ACS Sustainable Chemistry and Engineering. 2018;6(10):13358-13366.
doi:10.1021/acssuschemeng.8b03127.s006 .
Janković, Nenad Ž., Stefanović, Srđan M., Petronijević, Jelena, Joksimović, Nenad, Novaković, Slađana B., Bogdanović, Goran A., Muškinja, Jovana, Vraneš, Milan, Ratković, Zoran R., Bugarčić, Zorica M., "Supporting information for: Water-Tuned Tautomer-Selective Tandem Synthesis of the 5,6-Dihydropyrimidin-4(3 H )-ones, Driven under the Umbrella of Sustainable Chemistry" in ACS Sustainable Chemistry and Engineering, 6, no. 10 (2018):13358-13366,
https://doi.org/10.1021/acssuschemeng.8b03127.s006 . .
6
11

Acryloylferrocene as a convenient precursor of tetrahydropyrazolopyrazolones: [3+2] cycloaddition with N,N′ -Cyclic azomethine imines

Jovanović, Jovana P.; Novaković, Slađana B.; Bogdanović, Goran A.; Minić, Aleksandra; Pejović, Anka; Katanić, Jelena; Mihailović, Vladimir B.; Nastasijević, Branislav J.; Stevanović, Dragana D.; Damljanović, Ivan S.

(2018)

TY  - JOUR
AU  - Jovanović, Jovana P.
AU  - Novaković, Slađana B.
AU  - Bogdanović, Goran A.
AU  - Minić, Aleksandra
AU  - Pejović, Anka
AU  - Katanić, Jelena
AU  - Mihailović, Vladimir B.
AU  - Nastasijević, Branislav J.
AU  - Stevanović, Dragana D.
AU  - Damljanović, Ivan S.
PY  - 2018
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7635
AB  - AlCl3-Catalyzed {[}3 + 2] dipolar cycloaddition of the N,N'-cyclic azomethine imines to the acryloylferrocene enabling access to the series of 5-substituted 6-ferrocenoyl tetrahydropyrazolo {[}1,2-a]pyrazol-1(5H)-ones. This facile methodology shows high substituent tolerance. Furthermore, easy chromatographic separations afford isolation of the pure diastereoisomers. Optimized reaction conditions, spectroscopic and electrochemical characteristics of the reaction products are provided. The X-ray structural analyses of three cycloadducts were done and obtained results were compared with properties of reported N,N'-bicyclic systems those displayed conformational similarity. Antibacterial activities of all products against two Gram-positive and two Gram-negative bacterial strains were evaluated by the experimental methods. (c) 2018 Elsevier B.V. All rights reserved.
T2  - Journal of Organometallic Chemistry
T1  - Acryloylferrocene as a convenient precursor of tetrahydropyrazolopyrazolones: [3+2] cycloaddition with N,N′ -Cyclic azomethine imines
VL  - 860
SP  - 85
EP  - 97
DO  - 10.1016/j.jorganchem.2018.02.016
ER  - 
@article{
author = "Jovanović, Jovana P. and Novaković, Slađana B. and Bogdanović, Goran A. and Minić, Aleksandra and Pejović, Anka and Katanić, Jelena and Mihailović, Vladimir B. and Nastasijević, Branislav J. and Stevanović, Dragana D. and Damljanović, Ivan S.",
year = "2018",
abstract = "AlCl3-Catalyzed {[}3 + 2] dipolar cycloaddition of the N,N'-cyclic azomethine imines to the acryloylferrocene enabling access to the series of 5-substituted 6-ferrocenoyl tetrahydropyrazolo {[}1,2-a]pyrazol-1(5H)-ones. This facile methodology shows high substituent tolerance. Furthermore, easy chromatographic separations afford isolation of the pure diastereoisomers. Optimized reaction conditions, spectroscopic and electrochemical characteristics of the reaction products are provided. The X-ray structural analyses of three cycloadducts were done and obtained results were compared with properties of reported N,N'-bicyclic systems those displayed conformational similarity. Antibacterial activities of all products against two Gram-positive and two Gram-negative bacterial strains were evaluated by the experimental methods. (c) 2018 Elsevier B.V. All rights reserved.",
journal = "Journal of Organometallic Chemistry",
title = "Acryloylferrocene as a convenient precursor of tetrahydropyrazolopyrazolones: [3+2] cycloaddition with N,N′ -Cyclic azomethine imines",
volume = "860",
pages = "85-97",
doi = "10.1016/j.jorganchem.2018.02.016"
}
Jovanović, J. P., Novaković, S. B., Bogdanović, G. A., Minić, A., Pejović, A., Katanić, J., Mihailović, V. B., Nastasijević, B. J., Stevanović, D. D.,& Damljanović, I. S.. (2018). Acryloylferrocene as a convenient precursor of tetrahydropyrazolopyrazolones: [3+2] cycloaddition with N,N′ -Cyclic azomethine imines. in Journal of Organometallic Chemistry, 860, 85-97.
https://doi.org/10.1016/j.jorganchem.2018.02.016
Jovanović JP, Novaković SB, Bogdanović GA, Minić A, Pejović A, Katanić J, Mihailović VB, Nastasijević BJ, Stevanović DD, Damljanović IS. Acryloylferrocene as a convenient precursor of tetrahydropyrazolopyrazolones: [3+2] cycloaddition with N,N′ -Cyclic azomethine imines. in Journal of Organometallic Chemistry. 2018;860:85-97.
doi:10.1016/j.jorganchem.2018.02.016 .
Jovanović, Jovana P., Novaković, Slađana B., Bogdanović, Goran A., Minić, Aleksandra, Pejović, Anka, Katanić, Jelena, Mihailović, Vladimir B., Nastasijević, Branislav J., Stevanović, Dragana D., Damljanović, Ivan S., "Acryloylferrocene as a convenient precursor of tetrahydropyrazolopyrazolones: [3+2] cycloaddition with N,N′ -Cyclic azomethine imines" in Journal of Organometallic Chemistry, 860 (2018):85-97,
https://doi.org/10.1016/j.jorganchem.2018.02.016 . .
9
7
9

Synthesis, characterization, antioxidant and antimicrobial activity of novel 5-arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones

Pejović, Anka; Minić, Aleksandra; Jovanović, Jovana P.; Pešić, Marko S.; Ilić-Komatina, Danijela; Damljanović, Ivan S.; Stevanović, Dragana D.; Mihailović, Vladimir B.; Katanić, Jelena; Bogdanović, Goran A.

(2018)

TY  - JOUR
AU  - Pejović, Anka
AU  - Minić, Aleksandra
AU  - Jovanović, Jovana P.
AU  - Pešić, Marko S.
AU  - Ilić-Komatina, Danijela
AU  - Damljanović, Ivan S.
AU  - Stevanović, Dragana D.
AU  - Mihailović, Vladimir B.
AU  - Katanić, Jelena
AU  - Bogdanović, Goran A.
PY  - 2018
UR  - http://linkinghub.elsevier.com/retrieve/pii/S0022328X18303796
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7701
AB  - Synthesis of twenty novel 5-arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones has been achieved in good to excellent yields by the Knoevenagel condensation of 2-ferrocenyl-1,3-thiazolidin-4-ones with aromatic aldehydes. The reaction was performed by refluxing the mixture of reactants and potassium tert-butoxide in dioxane overnight. All new compounds were characterized by the IR and NMR spectral data, and their electrochemical properties were investigated using the cyclic voltammetry. The X-ray crystal structure of one of the representative thiazolidin-4(1H)-ones is also presented. All obtained products were evaluated for their in vitro antioxidant, antibacterial and antifungal activity.
T2  - Journal of Organometallic Chemistry
T1  - Synthesis, characterization, antioxidant and antimicrobial activity of novel 5-arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones
VL  - 869
SP  - 1
EP  - 10
DO  - 10.1016/j.jorganchem.2018.05.014
ER  - 
@article{
author = "Pejović, Anka and Minić, Aleksandra and Jovanović, Jovana P. and Pešić, Marko S. and Ilić-Komatina, Danijela and Damljanović, Ivan S. and Stevanović, Dragana D. and Mihailović, Vladimir B. and Katanić, Jelena and Bogdanović, Goran A.",
year = "2018",
abstract = "Synthesis of twenty novel 5-arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones has been achieved in good to excellent yields by the Knoevenagel condensation of 2-ferrocenyl-1,3-thiazolidin-4-ones with aromatic aldehydes. The reaction was performed by refluxing the mixture of reactants and potassium tert-butoxide in dioxane overnight. All new compounds were characterized by the IR and NMR spectral data, and their electrochemical properties were investigated using the cyclic voltammetry. The X-ray crystal structure of one of the representative thiazolidin-4(1H)-ones is also presented. All obtained products were evaluated for their in vitro antioxidant, antibacterial and antifungal activity.",
journal = "Journal of Organometallic Chemistry",
title = "Synthesis, characterization, antioxidant and antimicrobial activity of novel 5-arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones",
volume = "869",
pages = "1-10",
doi = "10.1016/j.jorganchem.2018.05.014"
}
Pejović, A., Minić, A., Jovanović, J. P., Pešić, M. S., Ilić-Komatina, D., Damljanović, I. S., Stevanović, D. D., Mihailović, V. B., Katanić, J.,& Bogdanović, G. A.. (2018). Synthesis, characterization, antioxidant and antimicrobial activity of novel 5-arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones. in Journal of Organometallic Chemistry, 869, 1-10.
https://doi.org/10.1016/j.jorganchem.2018.05.014
Pejović A, Minić A, Jovanović JP, Pešić MS, Ilić-Komatina D, Damljanović IS, Stevanović DD, Mihailović VB, Katanić J, Bogdanović GA. Synthesis, characterization, antioxidant and antimicrobial activity of novel 5-arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones. in Journal of Organometallic Chemistry. 2018;869:1-10.
doi:10.1016/j.jorganchem.2018.05.014 .
Pejović, Anka, Minić, Aleksandra, Jovanović, Jovana P., Pešić, Marko S., Ilić-Komatina, Danijela, Damljanović, Ivan S., Stevanović, Dragana D., Mihailović, Vladimir B., Katanić, Jelena, Bogdanović, Goran A., "Synthesis, characterization, antioxidant and antimicrobial activity of novel 5-arylidene-2-ferrocenyl-1,3-thiazolidin-4-ones" in Journal of Organometallic Chemistry, 869 (2018):1-10,
https://doi.org/10.1016/j.jorganchem.2018.05.014 . .
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Synthesis, structural and electrochemical characterization of novel 1,3-ketoureas bearing a ferrocenyl group

(2018)

TY  - JOUR
PY  - 2018
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7583
AB  - Twenty-two novel 1,3-ketourea derivatives bearing ferrocene moiety were synthesized in good-to-excellent yields (up to 99%) via simple and efficient protocol. This solvent- and catalyst-free synthesis was achieved by additions of different ferrocene-containing Mannich bases - 3-(arylamino)-1-ferrocenyl-propan-1-ones to phenyl isocyanate promoted only by ultrasound irradiations at ambient temperature. All synthesized 1-aryl-3-phenyl-1-(3-ferrocenyl-3-oxopropyl)ureas were characterized by standard spectral data (H-1 NMR, C-13 NMR and IR), and their electrochemical behavior were investigated by cyclic voltammetry. Detailed single-crystal X-ray diffraction analysis of three representative ferrocene-containing 1,3-ketoureas, among which one crystallized with two independent molecules in an asymmetric unit, were done. (C) 2017 Elsevier Ltd. All rights reserved.
T2  - Polyhedron
T1  - Synthesis, structural and electrochemical characterization of novel 1,3-ketoureas bearing a ferrocenyl group
VL  - 141
SP  - 343
EP  - 351
DO  - 10.1016/j.poly.2017.12.018
ER  - 
@article{
year = "2018",
abstract = "Twenty-two novel 1,3-ketourea derivatives bearing ferrocene moiety were synthesized in good-to-excellent yields (up to 99%) via simple and efficient protocol. This solvent- and catalyst-free synthesis was achieved by additions of different ferrocene-containing Mannich bases - 3-(arylamino)-1-ferrocenyl-propan-1-ones to phenyl isocyanate promoted only by ultrasound irradiations at ambient temperature. All synthesized 1-aryl-3-phenyl-1-(3-ferrocenyl-3-oxopropyl)ureas were characterized by standard spectral data (H-1 NMR, C-13 NMR and IR), and their electrochemical behavior were investigated by cyclic voltammetry. Detailed single-crystal X-ray diffraction analysis of three representative ferrocene-containing 1,3-ketoureas, among which one crystallized with two independent molecules in an asymmetric unit, were done. (C) 2017 Elsevier Ltd. All rights reserved.",
journal = "Polyhedron",
title = "Synthesis, structural and electrochemical characterization of novel 1,3-ketoureas bearing a ferrocenyl group",
volume = "141",
pages = "343-351",
doi = "10.1016/j.poly.2017.12.018"
}
(2018). Synthesis, structural and electrochemical characterization of novel 1,3-ketoureas bearing a ferrocenyl group. in Polyhedron, 141, 343-351.
https://doi.org/10.1016/j.poly.2017.12.018
Synthesis, structural and electrochemical characterization of novel 1,3-ketoureas bearing a ferrocenyl group. in Polyhedron. 2018;141:343-351.
doi:10.1016/j.poly.2017.12.018 .
"Synthesis, structural and electrochemical characterization of novel 1,3-ketoureas bearing a ferrocenyl group" in Polyhedron, 141 (2018):343-351,
https://doi.org/10.1016/j.poly.2017.12.018 . .
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Short Intramolecular O···O Contact in Some o -Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area

Bogdanović, Goran A.; Ostojić, Bojana D.; Novaković, Slađana B.

(2018)

TY  - JOUR
AU  - Bogdanović, Goran A.
AU  - Ostojić, Bojana D.
AU  - Novaković, Slađana B.
PY  - 2018
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/7659
AB  - Statistical analysis of data extracted from the Cambridge Structural Database (CSD) has been used to investigate the crystal structure properties of odialkoxybenzene derivatives, compounds containing two ether oxygen acceptors in ortho positions of benzene ring. It has been shown that in more than 90% of cases, the fragment has predictable geometrical characteristics where the two ether oxygens form short interatomic O center dot center dot center dot O contact (2.57 A in average), while O-substitutents take trans position, both approximately coplanar with the benzene ring. Such arrangement of oxygen acceptors produces a large and uniform area of the negative electrostatic potential suitable for multiple hydrogen bonding. The acceptor abilities of the O center dot center dot center dot O system have been investigated by the statistical CSD analysis. The ab initio estimation of the interaction energy in the dimer of o-dimethoxybenzene (DMB) and H2O, employed as a model system, is achieved via high-level electron correlation CCSD(T) calculation with the complete basis set extrapolation. The interaction energy is estimated to be 6.5 kcal/mol. The results indicate the existence of a very flat potential the region between methoxy oxygens and that DMB water is a highly flexible system. The structural role of the O center dot center dot center dot O acceptor system is particularly interesting considering its ability to form multiple hydrogen bonding
T2  - Crystal Growth and Design
T1  - Short Intramolecular O···O Contact in Some o -Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area
VL  - 18
IS  - 3
SP  - 1303
EP  - 1314
DO  - 10.1021/acs.cgd.7b00914
ER  - 
@article{
author = "Bogdanović, Goran A. and Ostojić, Bojana D. and Novaković, Slađana B.",
year = "2018",
abstract = "Statistical analysis of data extracted from the Cambridge Structural Database (CSD) has been used to investigate the crystal structure properties of odialkoxybenzene derivatives, compounds containing two ether oxygen acceptors in ortho positions of benzene ring. It has been shown that in more than 90% of cases, the fragment has predictable geometrical characteristics where the two ether oxygens form short interatomic O center dot center dot center dot O contact (2.57 A in average), while O-substitutents take trans position, both approximately coplanar with the benzene ring. Such arrangement of oxygen acceptors produces a large and uniform area of the negative electrostatic potential suitable for multiple hydrogen bonding. The acceptor abilities of the O center dot center dot center dot O system have been investigated by the statistical CSD analysis. The ab initio estimation of the interaction energy in the dimer of o-dimethoxybenzene (DMB) and H2O, employed as a model system, is achieved via high-level electron correlation CCSD(T) calculation with the complete basis set extrapolation. The interaction energy is estimated to be 6.5 kcal/mol. The results indicate the existence of a very flat potential the region between methoxy oxygens and that DMB water is a highly flexible system. The structural role of the O center dot center dot center dot O acceptor system is particularly interesting considering its ability to form multiple hydrogen bonding",
journal = "Crystal Growth and Design",
title = "Short Intramolecular O···O Contact in Some o -Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area",
volume = "18",
number = "3",
pages = "1303-1314",
doi = "10.1021/acs.cgd.7b00914"
}
Bogdanović, G. A., Ostojić, B. D.,& Novaković, S. B.. (2018). Short Intramolecular O···O Contact in Some o -Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area. in Crystal Growth and Design, 18(3), 1303-1314.
https://doi.org/10.1021/acs.cgd.7b00914
Bogdanović GA, Ostojić BD, Novaković SB. Short Intramolecular O···O Contact in Some o -Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area. in Crystal Growth and Design. 2018;18(3):1303-1314.
doi:10.1021/acs.cgd.7b00914 .
Bogdanović, Goran A., Ostojić, Bojana D., Novaković, Slađana B., "Short Intramolecular O···O Contact in Some o -Dialkoxybenzene Derivatives Generates Efficient Hydrogen Bonding Acceptor Area" in Crystal Growth and Design, 18, no. 3 (2018):1303-1314,
https://doi.org/10.1021/acs.cgd.7b00914 . .
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