Synthesis and antitumor activity of novel 2-thioxo-4-thiazolidinones with benzothiazole moieties

Following the reaction of benzothiazol-2-yl-hydrazine or (2-oxo-benzothiazol-3-yl)-acetic acid hydrazide with thiocarbonyl-bis-thioglycolic acid, 3-(benzothiazol-2-ylamino)-2 -thioxothiazolidin-4-one (1) and 2-(2-oxobenzothiazol-3-yl)-N-(4-oxo-2-hioxothiazolidin-3-yl) -acetamide (2) were synthesized, as starting compounds for obtaining new 5-arylidenederivatives (3-6) in Knoevenagel condensation with aromatic aldehydes and isatines. The synthesized compounds showed antitumor activity on renal cancer, non-small cell lung cancer and ovarian cancer cell lines. The most efficient anticancer agent, 2-{2-[3-(benzothiazol-2-ylamino)-4-oxo-2-thioxo-thiazolidin-5- ylidenemethyl] -4-chloro-phenoxy}-N-(4-methoxyphenyl)-acetamide 3d was found to be active with average values of -5.38 and -4.45 for logGI₅₀ and logTGI, respectively.