Synthesis and Cytotoxic Evaluation of Novel 1,2,3-Triazole-4-Linked (2E,6E)-2-Benzylidene-6-(4-nitrobenzylidene)cyclohexanones

This work describes the synthesis of novel 1,2,3-triazole-4-linked (2E,6E)-2-benzylidene-6-(4-nitrobenzylidene)cyclo-hexanones starting from cyclohexanone. 1-(Cyclohex-1-en-1-yl)piperidine, the enamine from cyclohexanone and piperidine, reacted with 4-nitrobenzaldehyde to obtain 2-(4-nitrobenzylidene)cyclohexanone. Condensation of the latter compound with (prop-2-yn-1-yloxy)benzaldehyde derivatives under acidic conditions gave (4-nitrobenzylidene)-[(prop-2-yn-1-yloxy)-benzylidene]cyclohexanones. Finally, ‘click reaction’ of these derivatives and various organic azides led to the title compounds. All compounds were examined by MTT assay for cytotoxic activity in one human breast cancer cell line, MDA-MB-231.