Discovery of anxiolytic 2-ferrocenyl-1,3-thiazolidin-4-ones exerting GABA(A) receptor interaction via the benzodiazepine-binding site
Samo za registrovane korisnike
2014
Autori
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.
Članak u časopisu (Objavljena verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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.
Ključne reči:
2-Ferrocenyl-1,3-thiazolidin-4-ones / Anxiolytic agents / Ligand docking / GABA(A) receptor complex / GABA(A) benzodiazepine-binding siteIzvor:
European Journal of Medicinal Chemistry, 2014, 83, 57-73Finansiranje / projekti:
- Nove elektrohemijske i hemijske metode u sintezi organskih jedinjenja od interesa za medicinu i hemiju materijala (RS-MESTD-Basic Research (BR or ON)-172034)
- Kombinatorne biblioteke heterogenih katalizatora, prirodnih proizvoda, modifikovanih prirodnih proizvoda i njihovih analoga: put ka novim biološki aktivnim agensima (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
Kolekcije
Institucija/grupa
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 . .