Synthesis and Antitumor Activity of Some New Fused Heterocyclic Compounds

Resumo

Reaction of thiopyrimidine derivative 3 with hydrozonoyl chlorides 4a–4e gives new fused heterocyclic compounds 7a–7e containing triazole ring. The latter demonstrates a wide range of biological activities. Thiazolone pyridopyrimidines 8, 9a, 9b are prepared by the reaction of thiopyrimidines with chloroacetic acid and different aromatic aldehydes in the presence of acetic anhydride. Bis-arylidene 2 reacts with malononitrile or ethyl cyanoacetate with formation of carbonitrile derivatives 10, 11. Reaction of bisarylidene 2 with phenyl hydrazine and hydrazine hydrate leads to diazole derivatives 12, 13. Structures of the new compounds are elucidated from IR, ¹H and ¹³C NMR, and mass spectra. All newly synthesized products are tested for antitumor activity on three human tumor cell lines, including prostatic adenocarcinoma (PC3), human colorectal carcinoma (HCT116), human liver hepatocellular carcinoma (HepG2) and breast carcinoma (MCF7). Compounds 2, 7a–7d demonstrate the considerable potency.