Synthesis and Cytotoxic Evaluation of Novel 1,2,3‐Triazole‐4‐Linked (2E,6E)‐2‐Benzylidene‐6‐(4‐nitrobenzylidene)cyclohexanones |
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| Authors: | Mohammad Mahdavi Maryam Akhbari Mina Saeedi Maryam Karimi Niloufar Foroughi Elahe Karimpour‐Razkenari Heshmatollah Alinezhad Alireza Foroumadi Abbas Shafiee Tahmineh Akbarzadeh |
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| Affiliation: | 1. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran;2. The Essential Oil Research Center, University of Kashan, Kashan, Iran;3. Faculty of Pharmacy, Medicinal Plants Research Center, Tehran University of Medical Sciences, Tehran, Iran;4. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran;5. Faculty of Chemistry, University of Mazandaran, Babolsar, Iran;6. +98‐21‐66461178;7. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran |
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| 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. |
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| Keywords: | (E,E)‐2‐Benzylidene‐6‐(4‐Nitrobenzylidene)cyclohexanones 1,2,3‐Triazoles Click chemistry Cyclohexanone Cytotoxic activity |
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