A new series of 3-substituted-thiazolyl-2-iminothiazolidin-4-ones were synthesized by nucleophilic substitution of p-substituted-thiazol-2-yl-chloroacetamides with potassium thiocyanide by cyclization. The starting material p-substituted-thiazol-2-yl-chloroacetamides were synthesized from p-substituted-thiazol-2-yl-amines with chloroacetyl chloride, which in turn was prepared from one pot reaction of substituted aryl acetophenone and amino group of thiourea. The title compounds were investigated for their anticonvulsant activity. Among the tested compounds, compound 3-(4-(4-fluorophenyl)thiazol-2-yl)-2-iminothiazolidin-4-one (16) emerged as the most active compound of the series, and it is moderately more potent than the reference standard diazepam.
A new series of 2‐(4‐dimethylaminophenyl)‐3‐substituted thiazolidin‐4‐one‐5‐yl‐acetyl acetamides/benzamides were synthesized by the nucleophilic substitution of 3‐substituted‐2‐(4‐dimethylaminophenyl)‐thiazolidin‐4‐one‐5‐yl‐acetylchloride with acetamide and benzamide. The starting material 3‐substituted‐2‐(4‐dimethylaminophenyl)‐thiazolidin‐4‐one‐5‐yl‐acetylchloride was synthesized from 3‐substituted‐2‐(4‐dimethylaminophenyl)‐thiazolidin‐4‐one‐5‐yl‐acetic acid, which in turn was prepared by one‐pot reaction of amino component, p‐dimethylamino benzaldehyde and mercapto succinic acid. The title compounds were investigated for their anticonvulsant activities; among the test compounds, compound 2‐(4‐dimethylaminophenyl)‐3‐phenylamino‐thiazolidine‐4‐one‐5‐yl‐acetylbenzamide (14) emerged as the most active compound of the series and as moderately more potent than the reference standard diazepam.
Synthesis and Pharmacological Investigation of 2-(4-Dimethylaminophenyl)--3,5-disubstituted Thiazolidin-4-ones as Anticonvulsants. -Among the title thiazolidones synthesized, benzamide (IXd) appears to be the most active compound. It is found to be moderately more potent than the reference diazepam. -(SENTHILRAJA, M.; ALAGARSAMY*, V.; Arch. Pharm. (Weinheim, Ger.) 345 (2012) 10, 827-833, http://dx.doi.org/10.1002/ardp.201200126 ; Med. Chem. Res. Lab., MNR Coll. Pharm., Fasalwadi, Sangareddy 502 294, India; Eng.) -A. Forchert
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