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Synthesis and Cytotoxic Evaluation of Novel 1,2,3-Triazole-4-Linked (2E,6E)-2-Benzylidene-6-(4-Nitrobenzylidene)Cyclohexanones Publisher



Mahdavi M1 ; Akhbari M2 ; Saeedi M3, 4 ; Karimi M2 ; Foroughi N2 ; Karimpourrazkenari E4 ; Alinezhad H5 ; Foroumadi A1 ; Shafiee A1 ; Akbarzadeh T4, 6
Authors

Source: Helvetica Chimica Acta Published:2016


Abstract

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. © 2016 Verlag Helvetica Chimica Acta AG, Zurich.
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