Synthesis of some 5‐arylidene‐2‐(4‐acetamidophenylimino)‐thiazolidin‐4‐one derivatives and exploring their breast anticancer activity
Hana M. Abumelha, Ali Saeed
Abstract
Abstract Ten 2‐(4‐acetamidophenylimino)‐5‐arylidenethiazolidin‐4‐one derivatives 6a‐k were synthesized and evaluated for their anticancer activity against MCF‐7 cell line (breast adenocarcinoma). The synthetic approach involves cyclocondensation of N , N′ ‐bis(4‐acetamidophenyl)‐thiourea (3) with ethyl bromoacetate in ethanol and sodium acetate to furnish the 2‐(4‐acetamidophenylimino)‐4‐thiazolidinone derivative 4 , which underwent Knoevenagel condensation reaction with some substituted aldehydes to afford the targeted 2‐(4‐acetamidophenylimino)‐5‐arylidenethiazolidin‐4‐ones 6a ‐ k . The 4‐chlorobenzylidene‐thiazolidin‐4‐one compound 6h exhibited strong inhibitory effect on the growth of breast cancer cell with IC 50 (58.33 ± 1.74μM), very close to that of the reference drug doxorubicin (IC 50 48.06 ± 0.36μM).