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E-Journal of Chemistry
Volume 6, Issue 2, Pages 495-503
http://dx.doi.org/10.1155/2009/645131

Synthesis and Anti-inflammatory Activity of Some Novel 2,4-Diaryl-3,5-bis(arylimino)-1,2,4-thiadiazolidine Derivatives

P. Venkatesh and S. N. Pandeya

Department of Pharmaceutical Sciences, Faculty of Health and Medical Sciences, Allahabad Agricultural Institute-Deemed University, Allahabad-211007, India

Received 1 July 2008; Accepted 21 August 2008

Copyright © 2009 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License , which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

A series of some novel 2,4-diaryl-3,5-bis(arylimino)-1,2,4-thiadiazolidine derivatives were synthesized and evaluated for anti-inflammatory activity. In the SAR study, the phenyl ring on 3 and 4 position of 1,2,4-thiadiazolidine ring substituted with chloro, nitro and methoxy groups showed better activity. The title compounds were synthesized from two steps; the first step involved the synthesis of diaryl substituted thioureas then, it was cyclised to give the 1,2,4-thiadiazole system in the presence of oxidizing agent (hydrogen peroxide and concentrated hydrochloric acid) in the second step. The purity of the synthesized compounds were judged by their C, H and N analysis and the structure was analyzed on the basis of IR, H1NMR, C13 NMR and Mass spectral data. The anti-inflammatory activity of new compounds was determined by λ-Carrageenan induced mice paw edema method using diclofenac sodium as a standard. Among the compounds tested four compounds, B2 (2,4-diphenyl-3,5-bis(3-nitrophenylimino)-1,2,4-thiadiazolidine), B4 (2,4-diphenyl-3,5-bis(3-chlorophenylimino)-1,2,4-thiadiazolidine), B6 (2,4-diphenyl-3,5-bis(4-methoxyphenylimino)-1,2,4-thiadiazolidine) and B7 (2,4-diphenyl-3,5-bis (2-methoxyphenylimino)-1,2,4-thiadiazolidine) were the most active compounds in these series.