Synthesis and antitumor activity of certain thienopyridine and pyridothienopyrimidine derivatives

ABSTRACT

A series of cyclopenteno[b] or tetrahydrobenzo[b]thiophenes, tetrahydrothieno[2,3-c]pyridines and tetrahydropyrido[4',3'4,5]thieno[2,3-d]pyrimidines was synthesized as antitumor agents. Most of the tested compounds showed cytotoxic effect [GI[50] < 10 [micro]M] against the growth of P388 leukemia cells. Ethyl2-phenylsulphonamido-4,5,6,7-tetrahydrobenzo[b]thiophen-3-carboxylate [lla], Ethyl 2-[4- bromo-phenylsulphonamido]-4,5,6,7-tetrahydrobenzo[b]thiophen-3-carboxylate [llb], Ethyl 2-[4-methylphenyl-sulphonamido]-4,5,6,7-tetrahydrobenzo[b]thiophen-3-carboxylate [IIc], Ethyl 2-[4-methoxybenzamido]-4,5,6,7 -tetrahydro[b]thiophen-3-carboxylate [IIIc] and N-[4-methylphenyl] N-[3-carbo-ethoxy-6-methyl-4,5,6,7-tetrahydrothieno[2,3-c] pyridin-2-yl] thiourea [lVc] showed strong potency [GI [50]; 0.8, 1.15,2.09, 1.3,2.25 [micro]M; respectively]. The detailed synthesis, spectroscopic and biological data are reported