Synthesis and evaluation of quinolinvinyl-phenoxy-1,2,3-triazole-acetamide hybrids against breast cancer

Abstract This work synthesized and evaluated a new series of quinolinvinyl-phenoxy-1,2,3-triazole-acetamide hybrids 9a-p against breast cancer cell lines, including MCF-7 and MDA-MB-231. Among 16 synthesized compounds, (E)-N-(4-chlorophenyl)-2-(4-((4-(2-(quinolin-2-yl)vinyl)phenoxy)methyl)-1H-1,2,3-...

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Main Authors: Maliheh Safavi, Aida Iraji, Sara Moghadam Farid, Mohammad Mahdavi, Samaneh Fattaheian-Dehkordi, Tahmineh Akbarzadeh, Mina Saeedi
Format: Article
Language:English
Published: Nature Portfolio 2025-05-01
Series:Scientific Reports
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Online Access:https://doi.org/10.1038/s41598-025-01051-w
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Summary:Abstract This work synthesized and evaluated a new series of quinolinvinyl-phenoxy-1,2,3-triazole-acetamide hybrids 9a-p against breast cancer cell lines, including MCF-7 and MDA-MB-231. Among 16 synthesized compounds, (E)-N-(4-chlorophenyl)-2-(4-((4-(2-(quinolin-2-yl)vinyl)phenoxy)methyl)-1H-1,2,3-triazol-1-yl)acetamide (9f) was the most active compound on both cell lines, with IC50 values of 16.84 (MCF-7) and 21.78 µM (MDA-MB-231). 3D cell culture was also performed by providing an accurate in vitro model to test the most potent analog on the cancerous spheroids. Additionally, compound 9f demonstrated significant apoptosis induction in MDA-MB-231 cells, as evidenced by Annexin V-FITC/PI assays, with an increase in total apoptotic cells. Over-activation of caspase-3 was also observed in cell-based assays, indicating a potential apoptotic mechanism. DFT analysis revealed favorable electronic properties and electrostatic potential distributions that suggest these compounds’ high reactivity and binding affinity with biological targets. These results underscore the promising anticancer potential of the synthesized hybrids for further therapeutic applications.
ISSN:2045-2322