SYNTHESIS AND EVALUATION OF ANTI-PROLIFERATIVE ACTIVITY OF NOVEL THIAZOLIDINONE DERIVATIVES

A series of, 2-thioxo-4-thiazolidinone (rhodanine) and 2,4-thiazolidine-dinone derivatives were synthesized by reacting 4-thiazolidine-dione/rhodanine moieties with 2-(4-formylphenoxy)-N-substituted-phenyl-acetamide, in equimolar proportions. The authentication of synthesized compounds was done by FTIR, ¹HNMR, and mass spectrophotometry. The derivatives, N-(phenyl) -2- {4-[ (4-oxo-2-thioxo-1, 3-thiazolidin-5-ylidene) methyl]phenoxy}acetamide and 2-{4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)-methyl]phenoxy}-N-(phenyl)-acetamide, were further screened for their anticancer properties against CEM cell lines. Cell viability was determined by trypan blue dye exclusion assay and cytotoxic effect of the compounds by MTT assay. The two derivatives, N-(phenyl)-2-{4-[(4-oxo-2-thioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy} acetamide and 2-{4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)-methyl]phenoxy}-N-(phenyl)-acetamide were found to be anti-proliferative in nature at 75 – 100 μM and 100 – 250 μM concentrations, respectively. Thus, it can be established that the rhodanine derivatives, N-(phenyl) -2- {4- [(4-oxo- 2- thioxo-1, 3-thiazolidin-5-ylidene) methyl]- phenoxy}acetamide and 2-{4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene) methyl] phenoxy}-N-(phenyl)-acetamide have anti-proliferative property against leukemic cell lines (lymphoblastic leukemia) and can be further optimized to improve its efficacy and safety.