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, Jessy Elizabeth Mathew

Research output: Contribution to journalArticlepeer-review

24 Citations (Scopus)

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-aminothiadiazoles were synthesized, which on reaction with substituted aromatic aldehydes and thioglycolic acid in the 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 the 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.

Original languageEnglish
Pages (from-to)397-408
Number of pages12
JournalActa Pharmaceutica
Volume63
Issue number3
DOIs
Publication statusPublished - 01-09-2013

All Science Journal Classification (ASJC) codes

  • Medicine(all)
  • Pharmacology
  • Pharmaceutical Science

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