Maria Apotrosoaei, I. Vasincu, S. Constantin
2014
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Journal
Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi
Abstract
AIM To design new thiazolidin-4-ones derivatives and to evaluate their potential antioxidant effects using in vitro methods. MATERIAL AND METHODS New ethyl esters of the 2-(R-phenyl)-4-oxo-thiazolidin-3-yl propionic acid were synthesized using "one step reaction" between different aromatic aldehydes, thioglycolic acid and beta-alanine ethyl ester hydrochloride. The antioxidant potential of the synthesized compounds was evaluated using the DPPH radical scavenging assay and phosphomolybdenum method. RESULTS Eight thiazolidine-4-one derivatives were obtained in good yields and high purity. The structure of the synthesized compounds was confirmed using IR spectroscopy. The evaluation of antioxidant activity showed that 2-[(4-NO2)-phenyl]-4-oxo-thiazolidin-3-yl propionic acid ethyl ester (compound 16) was the most active compound. For this derivative the DPPH radical scavenger activity (I% = 91.63% +/- 0.77) and the total antioxidant capacity (absorbance = 1.0691 +/- 0.0763) were similar with that of ascorbic acid used as standard antioxidant. CONCLUSIONS The antioxidant activity of the thiazolidine-4-one derivatives depends on the nature of the phenyl ring substituents, the NO2 and OH radicals having the most significant influence.