Synthesis, tautomeric structures, and antitumor activity of new perimidines

Abstract

New series of perimidine derivatives and fused perimidines were derived from the reaction of ketene aminals 1 and 2 with diazotized anilines or hydrazonoyl chlorides. In addition, 8,10-disubstituted-[1,2,4]triazolo[4,3-a] perimidines (20a-m) were prepared through the reaction of perimidine-2-thione (15) with hydrazonoyl chlorides. The structures of the newly synthesized compounds were established on the basis of spectral data and elemental analyses. Some products were investigated for their antitumor activities against the human breast cancer cell line MCF-7 and the liver carcinoma cell line HEPG-2, and the results of some derivatives showed promising activity. Four new series of substituted and fused perimidines were synthesized from the reaction of each of diazotized anilines and hydrazonoyl chlorides with heterocyclic ketene aminal and the reaction of 2-perimidene thione and hydrazonoyl chlorides. Some products were investigated for their antitumor activity against the human breast cancer cell line MCF-7 and the liver carcinoma cell line HEPG-2 and the results of some derivatives showed promising activity. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.