title: Synthesis, in vitro anticancer and antioxidant activity of thiadiazole substituted thiazolidin-4-ones.
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.
authors.forename: Alex
authors.initials: A
authors.lastname: Joseph
authors.forename: Chaitanyakumar S
authors.initials: CS
authors.lastname: Shah
authors.forename: Suthar Sharad
authors.initials: SS
authors.lastname: Kumar
authors.forename: Angel Treasa
authors.initials: AT
authors.lastname: Alex
authors.forename: Naseer
authors.initials: N
authors.lastname: Maliyakkal
authors.forename: Sudheer
authors.initials: S
authors.lastname: Moorkoth
authors.forename: Jessy Elizabeth
authors.initials: JE
authors.lastname: Mathew
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000975:Antioxidants / Q000138:chemical synthesis* / Q000494:pharmacology; D002626:Chemistry, Pharmaceutical / Q000379:methods*; D006801:Humans; D061986:MCF-7 Cells; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D045162:Thiazolidinediones / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D000975:Antioxidants; D013830:Thiadiazoles; D045162:Thiazolidinediones; C500090:thiazolidine-2,4-dione