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Discovery of anxiolytic 2-ferrocenyl-1,3-thiazolidin-4-ones exerting GABAA receptor interaction via the benzodiazepine-binding site.

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.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Pejović A,Denić MS,Stevanović D,Damljanović I,Vukićević M,Kostova K,Tavlinova-Kirilova M,Randjelović P,Stojanović NM,Bogdanović GA,Blagojević P,D'hooghe M,Radulović NS,Vukićević RD

doi

10.1016/j.ejmech.2014.05.062

subject

Has Abstract

pub_date

2014-08-18 00:00:00

pages

57-73

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(14)00486-3

journal_volume

83

pub_type

杂志文章

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