Synthesis,in Vitro Anticancer and Antioxidant Activity of Thiadiazole Substituted Thiazolidin-4-ones

Joseph, Alex and Shah, Chaitanyakumar S and Suthar, Sharad Kumar and Alex, Angel Treasa and Maliyakkal, Naseer and Moorkoth, Sudheer and Mathew, Jessy Elizabeth (2013) Synthesis,in Vitro Anticancer and Antioxidant Activity of Thiadiazole Substituted Thiazolidin-4-ones. Acta Pharmaceutica, 63 (3). pp. 397-408. ISSN 1846-9558

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Abstract

A series of novel 5-alkyl/aryl thiadiazole substituted thiazolidin-4-ones were synthesized by a two-step process. In the first step, 5-alkyl/aryl substituted 2-amino- thiadiazoles were synthesized, which on reaction with substituted aromatic aldehydes and thioglycolic acid in the presence of dicyclohexylcarbodiimide afforded thia - zolidin-4-ones. All the compounds were synthesized in fairly good yields and their structures were confirmed by spectral and physical data. The title compounds were screened for in vitro anti-proliferative activity on human breast adenocarcinoma cells (MCF-7) by MTT assay. Most of the derivatives showed an IC 50 less than 150 μmol L –1 . Among the compounds tested, 2-(2-nitrophe- nyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-thiazolidin -4-one ( 3f) , -(3-fluorophenyl)-3-(5-methyl-1,3,4-thiadiazol-2- -yl)-thiazolidin-4-one ( 3b ), and 2-(4-chlorophenyl)-3- -(5-methyl-1,3,4-thiadiazol-2-yl)-thiazolidin-4-one (3c) were found to be the most active derivatives with IC 50 values of 46.34, 66.84, and 60.71 μmol L –1 , respectively. Antioxidant studies of all the synthesized compounds were carried out by diphenylpicrylhydrazyl (DPPH) as - say. Among the compounds tested, 2-phenyl-3-(5-styryl- -1,3,4-thiadiazol-2-yl)-thiazolidin-4-one ( 3s ) elicited supe - rior antioxidant activity with IC 50 of 161.93 μmol L –1.

Item Type: Article
Uncontrolled Keywords: Thiadiazole; Thiazolidin-4-ones; Anticancer; An-tioxidant
Subjects: Pharmacy > MCOPS Manipal > Pharmaceutical Biotechnology
Pharmacy > MCOPS Manipal > Pharmaceutical Chemistry
Depositing User: KMC Manipal
Date Deposited: 07 Dec 2013 04:34
Last Modified: 07 Dec 2013 04:34
URI: http://eprints.manipal.edu/id/eprint/137925

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