Ferrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activity
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2018
Authors
Bugarinović, Jovana P.Pešić, Marko S.
Minić, Aleksandra
Katanić, Jelena
Ilić-Komatina, Danijela
Pejović, Anka
Mihailović, Vladimir B.
Stevanović, Dragana D.
Nastasijević, Branislav J.
Damljanović, Ivan S.
Article (Published version)
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© 2018 Elsevier Inc
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A series of ferrocenes which contain dinitrogen-fused pyrazolidinone ring were synthesized from acryloylferrocene (4) and N,N′‑cyclic azomethine imines (3). Novel 5‑aryl‑6‑ferrocenoyltetrahydropyrazolo[1,2‑a]pyrazol‑1(5H)-ones were obtained as mixtures of two diastereoisomers (trans and cis) which were separated and isolated as pure substances. Ortho-substituted N,N′‑cyclic azomethine imines 5-oxo-2-(2,4,6-trimethylbenzylidene)pyrazolidin-2-ium-1-ide (3e) and 2-(2-methoxybenzylidene)-5-oxopyrazolidin-2-ium-1-ide (3f) reacted stereoselectively affording only trans-6-ferrocenoyl-5-mesityltetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (5e) and 6-ferrocenoyl-5-(2-methoxyphenyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (5f). Ferrocenyl derivatives were screened for in vitro antioxidant and antifungal activities and excellent DPPH and ABTS radicals scavenging activity was observed with majority of tested 5‑aryl‑6‑ferrocenoyltetrahydropyrazolo[1,2‑a]pyrazol‑1(5H)-ones. Several tested compounds s...howed selective scavenging properties neutralizing ABTS•+ radical cations in contrast to inactivity toward DPPH[rad] radicals. Trans-5-aryl-6-ferrocenoyltetrahydropyrazolo[1,2-a]pyrazol-1(5H)-ones 5b, 5c, 5d, 5j as well as cis-6-ferrocenoyl-5-(p-tolyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6d) displayed fungal growth inhibition at low concentration against C. albicans and/or A. brasiliensis. Molecular docking studies revealed that the cis-6-ferrocenoyl-5-(4-nitrophenyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6l) and cis-6-ferrocenoyl-5-(naphthalen-2-yl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6n) have potential to become lead molecules in drug discovery process. © 2018 Elsevier Inc.
Keywords:
Ferrocenes / Pyrazolones / Antioxidant activity / Antibacterial activity / Antifungal activity / Cyclic voltammetrySource:
Journal of Inorganic Biochemistry, 2018, 189, 134-142Funding / projects:
- Simultaneous Bioremediation and Soilification of Degraded Areas to Preserve Natural Resources of Biologically Active Substances, and Development and Production of Biomaterials and Dietetic Products (RS-43004)
- Novel Electrochemical and Chemical Methods in Synthesis of Organic Compounds of Interest for Medicine and Material Chemistry (RS-172034)
DOI: 10.1016/j.jinorgbio.2018.09.015
ISSN: 0162-0134; 1873-3344
PubMed: 30265996
WoS: 000449036800014
Scopus: 2-s2.0-85053811669
URI
https://linkinghub.elsevier.com/retrieve/pii/S0162013418302472https://vinar.vin.bg.ac.rs/handle/123456789/7890
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VinčaTY - JOUR AU - Bugarinović, Jovana P. AU - Pešić, Marko S. AU - Minić, Aleksandra AU - Katanić, Jelena AU - Ilić-Komatina, Danijela AU - Pejović, Anka AU - Mihailović, Vladimir B. AU - Stevanović, Dragana D. AU - Nastasijević, Branislav J. AU - Damljanović, Ivan S. PY - 2018 UR - https://linkinghub.elsevier.com/retrieve/pii/S0162013418302472 UR - https://vinar.vin.bg.ac.rs/handle/123456789/7890 AB - A series of ferrocenes which contain dinitrogen-fused pyrazolidinone ring were synthesized from acryloylferrocene (4) and N,N′‑cyclic azomethine imines (3). Novel 5‑aryl‑6‑ferrocenoyltetrahydropyrazolo[1,2‑a]pyrazol‑1(5H)-ones were obtained as mixtures of two diastereoisomers (trans and cis) which were separated and isolated as pure substances. Ortho-substituted N,N′‑cyclic azomethine imines 5-oxo-2-(2,4,6-trimethylbenzylidene)pyrazolidin-2-ium-1-ide (3e) and 2-(2-methoxybenzylidene)-5-oxopyrazolidin-2-ium-1-ide (3f) reacted stereoselectively affording only trans-6-ferrocenoyl-5-mesityltetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (5e) and 6-ferrocenoyl-5-(2-methoxyphenyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (5f). Ferrocenyl derivatives were screened for in vitro antioxidant and antifungal activities and excellent DPPH and ABTS radicals scavenging activity was observed with majority of tested 5‑aryl‑6‑ferrocenoyltetrahydropyrazolo[1,2‑a]pyrazol‑1(5H)-ones. Several tested compounds showed selective scavenging properties neutralizing ABTS•+ radical cations in contrast to inactivity toward DPPH[rad] radicals. Trans-5-aryl-6-ferrocenoyltetrahydropyrazolo[1,2-a]pyrazol-1(5H)-ones 5b, 5c, 5d, 5j as well as cis-6-ferrocenoyl-5-(p-tolyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6d) displayed fungal growth inhibition at low concentration against C. albicans and/or A. brasiliensis. Molecular docking studies revealed that the cis-6-ferrocenoyl-5-(4-nitrophenyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6l) and cis-6-ferrocenoyl-5-(naphthalen-2-yl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6n) have potential to become lead molecules in drug discovery process. © 2018 Elsevier Inc. T2 - Journal of Inorganic Biochemistry T1 - Ferrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activity VL - 189 SP - 134 EP - 142 DO - 10.1016/j.jinorgbio.2018.09.015 ER -
@article{ author = "Bugarinović, Jovana P. and Pešić, Marko S. and Minić, Aleksandra and Katanić, Jelena and Ilić-Komatina, Danijela and Pejović, Anka and Mihailović, Vladimir B. and Stevanović, Dragana D. and Nastasijević, Branislav J. and Damljanović, Ivan S.", year = "2018", abstract = "A series of ferrocenes which contain dinitrogen-fused pyrazolidinone ring were synthesized from acryloylferrocene (4) and N,N′‑cyclic azomethine imines (3). Novel 5‑aryl‑6‑ferrocenoyltetrahydropyrazolo[1,2‑a]pyrazol‑1(5H)-ones were obtained as mixtures of two diastereoisomers (trans and cis) which were separated and isolated as pure substances. Ortho-substituted N,N′‑cyclic azomethine imines 5-oxo-2-(2,4,6-trimethylbenzylidene)pyrazolidin-2-ium-1-ide (3e) and 2-(2-methoxybenzylidene)-5-oxopyrazolidin-2-ium-1-ide (3f) reacted stereoselectively affording only trans-6-ferrocenoyl-5-mesityltetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (5e) and 6-ferrocenoyl-5-(2-methoxyphenyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (5f). Ferrocenyl derivatives were screened for in vitro antioxidant and antifungal activities and excellent DPPH and ABTS radicals scavenging activity was observed with majority of tested 5‑aryl‑6‑ferrocenoyltetrahydropyrazolo[1,2‑a]pyrazol‑1(5H)-ones. Several tested compounds showed selective scavenging properties neutralizing ABTS•+ radical cations in contrast to inactivity toward DPPH[rad] radicals. Trans-5-aryl-6-ferrocenoyltetrahydropyrazolo[1,2-a]pyrazol-1(5H)-ones 5b, 5c, 5d, 5j as well as cis-6-ferrocenoyl-5-(p-tolyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6d) displayed fungal growth inhibition at low concentration against C. albicans and/or A. brasiliensis. Molecular docking studies revealed that the cis-6-ferrocenoyl-5-(4-nitrophenyl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6l) and cis-6-ferrocenoyl-5-(naphthalen-2-yl)tetrahydropyrazolo[1,2-a]pyrazol-1(5H)-one (6n) have potential to become lead molecules in drug discovery process. © 2018 Elsevier Inc.", journal = "Journal of Inorganic Biochemistry", title = "Ferrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activity", volume = "189", pages = "134-142", doi = "10.1016/j.jinorgbio.2018.09.015" }
Bugarinović, J. P., Pešić, M. S., Minić, A., Katanić, J., Ilić-Komatina, D., Pejović, A., Mihailović, V. B., Stevanović, D. D., Nastasijević, B. J.,& Damljanović, I. S.. (2018). Ferrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activity. in Journal of Inorganic Biochemistry, 189, 134-142. https://doi.org/10.1016/j.jinorgbio.2018.09.015
Bugarinović JP, Pešić MS, Minić A, Katanić J, Ilić-Komatina D, Pejović A, Mihailović VB, Stevanović DD, Nastasijević BJ, Damljanović IS. Ferrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activity. in Journal of Inorganic Biochemistry. 2018;189:134-142. doi:10.1016/j.jinorgbio.2018.09.015 .
Bugarinović, Jovana P., Pešić, Marko S., Minić, Aleksandra, Katanić, Jelena, Ilić-Komatina, Danijela, Pejović, Anka, Mihailović, Vladimir B., Stevanović, Dragana D., Nastasijević, Branislav J., Damljanović, Ivan S., "Ferrocene-containing tetrahydropyrazolopyrazolones: Antioxidant and antimicrobial activity" in Journal of Inorganic Biochemistry, 189 (2018):134-142, https://doi.org/10.1016/j.jinorgbio.2018.09.015 . .