Heteroannelation of cyclic ketones: Synthesis, characterization and antitumor evaluation of some condensed azine derivatives

Abstract

A series of pyrimidine and thiazine derivatives synthesized by one pot reaction of cyclopentanone with a mixture of an aromatic aldehyde namely o-anisaldehyde and different ureas namely urea, guanidine and thiourea, respectively. Furthermore, cycloaddition reaction of active methylene reagents namely acetyl acetone, malononitrile, ethyl cyanoacetate, cyanoacetamide and N-phenyl cyanoacetamide with 2,6-bis(2-methoxybenzylidene)-cyclohexanone afforded chromene and quinoline derivatives in basic medium.  The antitumor evaluation of some new compounds against three human cell lines namely MCF-7, NCI-H460 and SF-268 showed significant and moderate activity compared with the positive control doxorubicin.