5‐Arylidene‐2‐(4‐hydroxyphenyl)aminothiazol‐4(5H)‐ones with selective inhibitory activity against some leukemia cell lines

Abstract The data on the pharmacology of 4‐thiazolidinones showed that 5‐ene‐2‐(imino)amino‐4‐thiazolidinones are likely to comprise one of the most promising groups of compounds possessing anticancer properties. A series of 5‐arylidene‐2‐(4‐hydroxyphenyl)aminothiazol‐4(5 H )‐ones was designed, synthesized, and studied against 10 leukemia cell lines, including the HL‐60, Jurkat, K‐562, Dami, KBM‐7, and some Ba/F3 cell lines. The structure–activity relationship analysis shows that almost all tested 5‐arylidene‐2‐(4‐hydroxyphenyl)aminothiazol‐4(5 H )‐ones were characterized by ІС 50 values lower or comparable to that of the control drug chlorambucil. Among the tested compounds, (5 Z )‐5‐(2‐methoxybenzylidene)‐ ( 12 ), (5 Z )‐(2‐ethoxybenzylidene)‐ ( 21 ), (5 Z )‐5‐(2‐benzyloxybenzylidene)‐ ( 25 ), and (5 Z )‐5‐(2‐allyloxybenzylidene)‐2‐(4‐hydroxyphenylamino)thiazol‐4(5 H )‐ones ( 28 ) possessed the highest antileukemic activity at submicromolar concentrations (ІС 50 = 0.10–0.95 µM).