Synthesis, characterization and in vitro anticancer activity of thiabendazole-derived 1,2,3-triazole derivatives

A series of thiabendazole-derived 1,2,3-triazole compounds were synthesized in good yields via 1,3-dipolar cycloaddition through click chemistry approach using different chain alkyl azides with 4-(1-(prop-2-yn-1-yl)benzimidazole-2-yl)thiazole in the presence of copper( i ) catalyst. These compounds...

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Bibliographic Details
Published in:New journal of chemistry 2020-01, Vol.44 (28), p.12099-12106
Main Authors: El Bourakadi, Khadija, Mekhzoum, Mohamed El Mehdi, Saby, Charles, Morjani, Hamid, Chakchak, Hind, Merghoub, Nawal, Qaiss, Abou el kacem, Bouhfid, Rachid
Format: Article
Language:English
Subjects:
Anticancer properties
Apoptosis
Biotechnology
Cancer
Cell death
Chemical synthesis
Copper compounds
Cycloaddition
Mass spectrometry
NMR
Nuclear magnetic resonance
Triazoles
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Summary:A series of thiabendazole-derived 1,2,3-triazole compounds were synthesized in good yields via 1,3-dipolar cycloaddition through click chemistry approach using different chain alkyl azides with 4-(1-(prop-2-yn-1-yl)benzimidazole-2-yl)thiazole in the presence of copper( i ) catalyst. These compounds were characterized on the basis of FT-IR, 1 H NMR, 13 C NMR as well as mass spectrometry. The newly synthesized compounds were screened for their in vitro antiproliferative activity against a panel of three human cancer cell lines (HT29, MDA-MB-231 and SKBR3). Compound 4g exhibited significant activity against all the cell lines tested, with IC 50 values ranging from 1.28 and 7.72 μg mL −1 , inducing caspases 3 and 7, which further confirms the contribution of apoptotic cell death in MCF-7 and MDA-MB-231 cells. This work further demonstrates the anticancer properties of 4g , inducing apoptotic cell death, and the structure activity association is also discussed. This product could be a promising chemotherapeutic agent for cancer treatment.
ISSN:1144-0546
1369-9261
DOI:10.1039/C9NJ05685H