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 IC50 (58.33 ± 1.74μM), very close to that of the reference drug doxorubicin (IC50 48.06 ± 0.36μM).
Amination of α,α‐diaminoketones 1 by 4,5‐dimethyl‐o‐phenylenediamine gave 6,7‐dimethyl‐2‐phenylquinoxaline (II) in a high yield. The reaction may occur through formation of α‐ketoazomethine III. The α,α‐di‐aminoketones were obtained by condensation of phenylglyoxal and substituted anilines.
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