Synthesis and antiproliferative activity of diethyl 5- acetyl-4-methyl- 6-(2-fluorophenylimino)-6H-thiopyran- 2,3-dicarboxylate (3TM)

Diethyl 5-acetyl-4-methyl-6-(2-fluorophenylimino)-6H-thiopyran-2,3-dicarboxylate (3TM) was synthesized and the antiproliferative activity of 3TM is reported here. Compound 3TM inhibits the growth of human colon cancer HCT-15 with an IC50 value of 4.5 μM and breast cancer MCF-7 with an IC50 value of 7 μM in a dose/time dependent manner by using sulforhodamine B assay. Moreover, suppression of clonogenic activity occurs after exposure to 3TM at a concentration of 3 μM for HCT-15 and of 5 μM for MCF-7. The effect of ligand complexation on DNA structure led to the overall affinity constant of K3M-DNA = 2.4 x 104 M-1.Key words: Diethyl 5-acetyl-4-methyl-6-(2-fluorophenylimino)-6H-thiopyran-2,3-dicarboxylate (3TM), synthesis, antiproliferative activity