TY  - JOUR
AU  - Minić, Aleksandra
AU  - Stevanović, Dragana D.
AU  - Vukićević, Mirjana
AU  - Bogdanović, Goran A.
AU  - D'hooghe, Matthias
AU  - Radulović, Niko S.
AU  - Vukićević, Rastko D.
PY  - 2017
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/1797
AB  - A series of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines were synthesized in high-to-excellent yields (up to 99%) starting from the corresponding ferrocenoylethyl aryl amines. These Mannich bases were reduced (NaBH4) to the corresponding 3-(arylamino)-1-ferrocenylpropan-1-ols and submitted to an intramolecular cyclization prompted by acetic acid, proceeding via the corresponding alpha-ferrocenyl carbenium ion intermediates. Subsequently, the obtained tetrahydroquinolines were smoothly oxidized (aromatized) by means of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to provide the corresponding 4-ferrocenylquinolines (up to 93%). (C) 2017 Elsevier Ltd. All rights reserved.
T2  - Tetrahedron
T1  - Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates
VL  - 73
IS  - 44
SP  - 6268
EP  - 6274
DO  - 10.1016/j.tet.2017.09.014
ER  - 

@article{
author = "Minić, Aleksandra and Stevanović, Dragana D. and Vukićević, Mirjana and Bogdanović, Goran A. and D'hooghe, Matthias and Radulović, Niko S. and Vukićević, Rastko D.",
year = "2017",
abstract = "A series of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines were synthesized in high-to-excellent yields (up to 99%) starting from the corresponding ferrocenoylethyl aryl amines. These Mannich bases were reduced (NaBH4) to the corresponding 3-(arylamino)-1-ferrocenylpropan-1-ols and submitted to an intramolecular cyclization prompted by acetic acid, proceeding via the corresponding alpha-ferrocenyl carbenium ion intermediates. Subsequently, the obtained tetrahydroquinolines were smoothly oxidized (aromatized) by means of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to provide the corresponding 4-ferrocenylquinolines (up to 93%). (C) 2017 Elsevier Ltd. All rights reserved.",
journal = "Tetrahedron",
title = "Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates",
volume = "73",
number = "44",
pages = "6268-6274",
doi = "10.1016/j.tet.2017.09.014"
}

Minić, A., Stevanović, D. D., Vukićević, M., Bogdanović, G. A., D'hooghe, M., Radulović, N. S.,& Vukićević, R. D.. (2017). Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates. in Tetrahedron, 73(44), 6268-6274.
https://doi.org/10.1016/j.tet.2017.09.014

Minić A, Stevanović DD, Vukićević M, Bogdanović GA, D'hooghe M, Radulović NS, Vukićević RD. Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates. in Tetrahedron. 2017;73(44):6268-6274.
doi:10.1016/j.tet.2017.09.014 .

Minić, Aleksandra, Stevanović, Dragana D., Vukićević, Mirjana, Bogdanović, Goran A., D'hooghe, Matthias, Radulović, Niko S., Vukićević, Rastko D., "Synthesis of novel 4-ferrocenyl-1,2,3,4-tetrahydroquinolines and 4-ferrocenylquinolines via alpha-ferrocenyl carbenium ions as key intermediates" in Tetrahedron, 73, no. 44 (2017):6268-6274,
https://doi.org/10.1016/j.tet.2017.09.014 . .

TY  - JOUR
AU  - Pejović, Anka
AU  - Denic, Marija S.
AU  - Stevanović, Dragana D.
AU  - Damljanović, Ivan S.
AU  - Vukićević, Mirjana
AU  - Kostova, Kalina
AU  - Tavlinova-Kirilova, Maya
AU  - Randjelovi, Pavle
AU  - Stojanović, Nikola M.
AU  - Bogdanović, Goran A.
AU  - Blagojevic, Polina
AU  - D'hooghe, Matthias
AU  - Radulović, Niko S.
AU  - Vukićević, Rastko D.
PY  - 2014
UR  - https://vinar.vin.bg.ac.rs/handle/123456789/76
AB  - Herein, we report on the synthesis, spectral, crystallographic and electrochemical properties of a small library of N-substituted 2-ferrocenyl-1,3-thiazolidin-4-ones, designed as novel GABA(A) benzodiazepine-binding site ligands. The anxiolytic properties of the title compounds were evaluated in several different in vivo models, whereas the involvement of the GABAA receptor complex in the activity of the most potent compound, 2-ferrocenyl-3-(4-methoxyphenylethyl)-1,3-thiazolidin-4-one, was inferred from experiments with known GABA(A)-targeting agents. Ligand docking experiments revealed that the high, dose-dependent, anxiolytic activity of the new compounds might be due to their favorable interactions with the benzodiazepine-binding site of the GABA(A) receptor complex. The incorporation of the ferrocene core and fine tuning of the distance between the thiazolidinone core and an additional aromatic ring were judged to be crucial structural requirements for the observed anxiolytic effect. (C) 2014 Elsevier Masson SAS. All rights reserved.
T2  - European Journal of Medicinal Chemistry
T1  - Discovery of anxiolytic 2-ferrocenyl-1,3-thiazolidin-4-ones exerting GABA(A) receptor interaction via the benzodiazepine-binding site
VL  - 83
SP  - 57
EP  - 73
DO  - 10.1016/j.ejmech.2014.05.062
ER  - 

@article{
author = "Pejović, Anka and Denic, Marija S. and Stevanović, Dragana D. and Damljanović, Ivan S. and Vukićević, Mirjana and Kostova, Kalina and Tavlinova-Kirilova, Maya and Randjelovi, Pavle and Stojanović, Nikola M. and Bogdanović, Goran A. and Blagojevic, Polina and D'hooghe, Matthias and Radulović, Niko S. and Vukićević, Rastko D.",
year = "2014",
abstract = "Herein, we report on the synthesis, spectral, crystallographic and electrochemical properties of a small library of N-substituted 2-ferrocenyl-1,3-thiazolidin-4-ones, designed as novel GABA(A) benzodiazepine-binding site ligands. The anxiolytic properties of the title compounds were evaluated in several different in vivo models, whereas the involvement of the GABAA receptor complex in the activity of the most potent compound, 2-ferrocenyl-3-(4-methoxyphenylethyl)-1,3-thiazolidin-4-one, was inferred from experiments with known GABA(A)-targeting agents. Ligand docking experiments revealed that the high, dose-dependent, anxiolytic activity of the new compounds might be due to their favorable interactions with the benzodiazepine-binding site of the GABA(A) receptor complex. The incorporation of the ferrocene core and fine tuning of the distance between the thiazolidinone core and an additional aromatic ring were judged to be crucial structural requirements for the observed anxiolytic effect. (C) 2014 Elsevier Masson SAS. All rights reserved.",
journal = "European Journal of Medicinal Chemistry",
title = "Discovery of anxiolytic 2-ferrocenyl-1,3-thiazolidin-4-ones exerting GABA(A) receptor interaction via the benzodiazepine-binding site",
volume = "83",
pages = "57-73",
doi = "10.1016/j.ejmech.2014.05.062"
}

Pejović, A., Denic, M. S., Stevanović, D. D., Damljanović, I. S., Vukićević, M., Kostova, K., Tavlinova-Kirilova, M., Randjelovi, P., Stojanović, N. M., Bogdanović, G. A., Blagojevic, P., D'hooghe, M., Radulović, N. S.,& Vukićević, R. D.. (2014). Discovery of anxiolytic 2-ferrocenyl-1,3-thiazolidin-4-ones exerting GABA(A) receptor interaction via the benzodiazepine-binding site. in European Journal of Medicinal Chemistry, 83, 57-73.
https://doi.org/10.1016/j.ejmech.2014.05.062

Pejović A, Denic MS, Stevanović DD, Damljanović IS, Vukićević M, Kostova K, Tavlinova-Kirilova M, Randjelovi P, Stojanović NM, Bogdanović GA, Blagojevic P, D'hooghe M, Radulović NS, Vukićević RD. Discovery of anxiolytic 2-ferrocenyl-1,3-thiazolidin-4-ones exerting GABA(A) receptor interaction via the benzodiazepine-binding site. in European Journal of Medicinal Chemistry. 2014;83:57-73.
doi:10.1016/j.ejmech.2014.05.062 .

Pejović, Anka, Denic, Marija S., Stevanović, Dragana D., Damljanović, Ivan S., Vukićević, Mirjana, Kostova, Kalina, Tavlinova-Kirilova, Maya, Randjelovi, Pavle, Stojanović, Nikola M., Bogdanović, Goran A., Blagojevic, Polina, D'hooghe, Matthias, Radulović, Niko S., Vukićević, Rastko D., "Discovery of anxiolytic 2-ferrocenyl-1,3-thiazolidin-4-ones exerting GABA(A) receptor interaction via the benzodiazepine-binding site" in European Journal of Medicinal Chemistry, 83 (2014):57-73,
https://doi.org/10.1016/j.ejmech.2014.05.062 . .