Discovery of anxiolytic 2-ferrocenyl-1,3-thiazolidin-4-ones exerting GABA(A) receptor interaction via the benzodiazepine-binding site
Само за регистроване кориснике
2014
Аутори
Pejović, AnkaDenic, 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.
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
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 effec...t. (C) 2014 Elsevier Masson SAS. All rights reserved.
Кључне речи:
2-Ferrocenyl-1,3-thiazolidin-4-ones / Anxiolytic agents / Ligand docking / GABA(A) receptor complex / GABA(A) benzodiazepine-binding siteИзвор:
European Journal of Medicinal Chemistry, 2014, 83, 57-73Финансирање / пројекти:
- Нове електрохемијске и хемијске методе у синтези органских једињења од интереса за медицину и хемију материјала (RS-MESTD-Basic Research (BR or ON)-172034)
- Комбинаторне библиотеке хетерогених катализатора, природних производа, модификованих природних производа и њихових аналога: пут ка новим биолошки активним агенсима (RS-MESTD-Basic Research (BR or ON)-172061)
DOI: 10.1016/j.ejmech.2014.05.062
ISSN: 0223-5234; 1768-3254
PubMed: 24950490
WoS: 000340689600006
Scopus: 2-s2.0-84902679997
Колекције
Институција/група
VinčaTY - 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 . .