Microwave-Assisted Synthesis, Antimicrobial and Cytotoxic Activities of Some 4-Thioxo-Thiazolidine-2-One Derivatives

Shankar      G. Alegaon; Kallanagouda      R. Alagawadi

Abstract

A series of (Z)-5-arylidene-4-thioxo-thiazolidine-2-ones (4a-o) were synthesized using microwave irradiation technique. The structures of the newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR spectral studies and elemental analysis. All compounds were evaluated for their preliminary in vitro antimicrobial and cytotoxic activities. The investigation of antimicrobial activity profile revealed that compounds 4d, 4f, 4g, and 4h exhibited marked activity against S. aureus and E. faecalis as compared with the standard while compounds 4d and 4h exhibited good antifungal activities against C. albicans, A. flavus, A. niger and C. neoformans. In preliminary MTT cytotoxicity studies, the (Z)-5- arylidene-4-thioxo-thiazolidine-2-one derivatives (4k, 4l and 4m) were found most potent. Compound 4m inhibited proliferation of HeLa, HT29, A549 and MCF-7 cell lines with an IC50 values of 23, 22, 20 and 20 μM, respectively.

Keywords: Antimicrobial activity, Cytotoxic activity, Microwave irradiation, Thiazolidine-2,4-dione, 4-Thioxo-thiazolidine-2-one, anticancer therapeutic agents, anticancer cancer agents, secondary malignancy, antihyperglycemic, Lawesson's Reagent, thiazolidinedione ring, Staphylococcus aureus, Enterococcus faecalis, Ampicillin, antifungal assay