Synthesis, Structure and Biological Activity of 2-[2-(4-Fluorobenzylidene)hydrazinyl]-4-(1-methyl-1H-indol-3-yl)thieno[3,2-d]pyrimidine

The title compound 2-[2-(4-fluorobenzylidene)hydrazinyl]-4-(1-methyl-1H-indol-3-yl)thieno[3,2-d] pyrimidine (8) was synthesized by the condensation of 4-fluorobenzaldehyde (7) with 2-hydrazinyl-4-(1-methyl-1H-indol-3-yl)thienop,2-dlpyrimidine (6). This intermediate was prepared from methyl 3-aminothiophene-2-carboxylate (1) by the condensation with urea, chlorination with phosphorus oxychloride and then condensation with hydrazine hydrate. The crystal of 8 belongs to monoclinic system, space group P2(1)/c with a = 14.0453(18), b = 17.436(2), c = 18.0982(17) angstrom and beta = 122.969(7)degrees. In addition, 8 possesses marked inhibition against the proliferation of human colon cancer cell line HT-29 (IC50 = 6.09 mu M) and human gastric cancer cell line MKN45 (IC50 = 3.04 mu M), displaying promising anticancer activity.