Acta Pharm. 63 (2013) 397-408
Original research paper
Synthesis, in vitro anticancer and antioxidant activity of thiadiazole substituted thiazolidin-4-ones
ALEX JOSEPH, CHAITANYAKUMAR S. SHAH, SUTHAR SHARAD KUMAR, ANGEL TREASA ALEX, NASEER MALIYAKKAL, SUDHEER MOORKOTH and JESSY ELIZABETH MATHEW
Manipal College of Pharmaceutical Sciences, Manipal University, Manipal, India
Accepted May 13, 2013
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 presence of dicyclohexylcarbodiimide afforded thiazolidin-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 IC50 less than 150 µmol L–1. Among the compounds tested, 2-(2-nitrophenyl)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-thiazolidin-4-one (3f), 2-(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 most active derivatives with IC50 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) assay. Among the compounds tested, 2-phenyl-3-(5-styryl-1,3,4-thiadiazol-2-yl)-thiazolidin-4-one (3s) elicited superior antioxidant activity with IC50 of 161.93 µmol L–1.
Keywords: thiadiazole, thiazolidin-4-ones, anticancer, antioxidant