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

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(5H)-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(5H)-ones were characterized by CYRILLIC CAPITAL LETTER BYELORUSSIAN-UKRAINIAN IC50 values lower or comparable to that of the control drug chlorambucil. Among the tested compounds, (5Z)-5-(2-methoxybenzylidene)- (12), (5Z)-(2-ethoxybenzylidene)- (21), (5Z)-5-(2-benzyloxybenzylidene)- (25), and (5Z)-5-(2-allyloxybenzylidene)-2-(4-hydroxyphenylamino)thiazol-4(5H)-ones (28) possessed the highest antileukemic activity at submicromolar concentrations (CYRILLIC CAPITAL LETTER BYELORUSSIAN-UKRAINIAN IC50 = 0.10-0.95 mu M).

Automated summary

Research suggests that 5-arylidyne-2-(4-hydroxyphenyl)aminothiazol-4(5H)-ones may have anticancer properties, with compounds like (5Z)-5-(2-methoxybenzylidene) demonstrating high antileukemic activity at submicromolar concentrations comparable to or lower than chlorambucil.