Absence of antidiabetic activity in some novel thiazolidinone derivatives

Abstract

Aim: It was aimed to synthesise some novel thiazolidinone derivatives and assess them
for antidiabetic activity. Material and Methods: A series of substituted 5-ethylidene2-(phenylimino) thiazolidin-4-ones were prepared by using phenylthiourea (I) as a
starting material. Phenylthiourea on reaction with ethylchloroacetate, in the presence
of ethanol and fused sodium acetate, gave 2-(phenylimino) thiazolidin-4-one (II), and
2-(phenylimino) thiazolidin-4-one on further reaction with substituted benzaldehyde
gave substituted 5-ethylidene-2- (phenylimino) thiazolidin-4-one (III – XVIII). The
synthesized compounds were authenticated on the basis of elemental analysis, IR, 1H
NMR, and Mass spectral analysis and some of the compounds were selected on the
basis of a literature review, to evaluate them for their antidiabetic activity. Results and
Conclusion: All The tested compounds 5-(4-fluorobenzylidene)-2-(phenylimino)
thiazolidin-4-on (VII) and 5-(4-Methylbenzylidene)-2-(phenylimino)thiazolidin-4-one
(X), 5-(2, 4-dinitrobenzylidene)-2-(phenylamino) thiazolidin-4-one (XVII) were found
to be ineffective in lowering the blood glucose level.