SYNTHESIS AND CHARACTERIZATION OF NOVEL 3-(AMINOMETHYL)-5- BENZYLIDENETHIAZOLIDINE-2,4-DIONE DERIVATIVES AS ANTICANCER AGENTS

Abstract

Thiazolidine-2, 4-dione (TZD) is a vital nucleus in heterocyclic chemistry. Novel 3-(aminomethyl)-5- benzylidenethiazolidine-2,4-dione derivatives were synthesized and characterized by 1H NMR, IR and Mass spectroscopy. The compounds wer synthesized by knoevenagel condensation with cyclization reaction and evaluated for anticancer activity against human cancer cell lines of HeLa (Cervical cancer cells) and HCT-8 (Colon carcinoma) using sulforhodamine B (SRB) method. Compound 3i was the most potent derivative of the series against both cell lines HeLa and HCT-8 with IC50 value of 0.007 μM and 0.001 μM, consecutively. By comparing the activities of potent compounds (3a, 3b, 3f, 3g, 3i, 3n, 3q) with other derivatives, it was revealed that the presence of electronegative groups at C-2 and C-3 positions of phenyl ring confers the highest cytotoxic activity against Cervical cancer and Colon carcinoma cell lines. The physicochemical parameters of these compounds followed the Lipinski rule of five.