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

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.

An Overview of Recent Advances in the Applications of Click Chemistry in the Synthesis of Bioconjugates with Anticancer Activities

“…Akbarzadeh et al . synthesized a series of novel 1,2,3‐triazole‐4‐linked (2 E ,6 E )‐2‐benzylidene‐6‐(4‐nitrobenzylidene)cyclohexanones ( 12 ) by the procedure outlined in Scheme .…”

1,2,3‐Triazole Tagged 3H‐Pyrano[2,3‐d]pyrimidine‐6‐carboxylate Derivatives: Synthesis, in Vitro Cytotoxicity, Molecular Docking and DNA Interaction Studies

“…They have received much attention of researchers because of their high effectiveness, low toxicity and wide applications in medicinal chemistry . 1,2,3‐Triazole played an important role in agrochemical and pharmaceuticals such as anticancer, anti‐inflammatory, [ ][ ] antibacterial, antiviral, anti‐HIV, fungicidal and insecticidal . For example, the triazole derivative carboxyamidotriazole 5 is an angiogenesis inhibitor useful in cancer therapy .…”

Novel quinazolin‐4(3H)‐one linked to 1,2,3‐triazoles: Synthesis and anticancer activity

“…As newly discovered, hybrid compounds have overcome many difficulties associated with conventional drugs; sideeffects and multidrug resistance (MDR), [13] here, in continuation of our efforts [14][15][16][17] to develop anticancer agents, we synthesized novel quinazolin-4(3H)-one linked to 1,2,3-triazoles and evaluated for their cytotoxicity against human breast, lung, and prostate cancer cell lines ( Figure 1). All required steps for the preparation of desired compounds 6 were outlined in Scheme 1.…”