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Title: Discovery of anxiolytic 2-ferrocenyl-1,3-thiazolidin-4-ones exerting GABA<inf>A</inf> receptor interaction via the benzodiazepine-binding site
Authors: Pejović, Anka
Denić M.
Stevanović, Dragana
Damljanović, Ivan
Vukićević, Miomir
Kostova K.
Tavlinova-Kirilova M.
Randjelovic, Pavle
Stojanovic, Nikola
Bogdanovic, Goran A.
Blagojevic, Polina
D'hooghe, Matthias
Radulovic, Niko
Vukicevic R.
Journal: European Journal of Medicinal Chemistry
Issue Date: 18-Aug-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 GABAA 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 GABAA-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 GABAA 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. © 2014 Elsevier Masson SAS. All rights reserved.
Type: Article
DOI: 10.1016/j.ejmech.2014.05.062
ISSN: 02235234
SCOPUS: 84902679997
Appears in Collections:Faculty of Science, Kragujevac
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