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Synthesis of Indole-1,3,4-Oxadiazole Based Sulfonyl 1,2,3-Triazoles as Potent Anticancer and EGFR Inhibitors

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Abstract

Herein, we synthesized some new indole-1,3,4-oxadiazole based sulfonyl 1,2,3-triazoles via a click chemistry approach and then characterized their structures by NMR, mass, and CHN analysis techniques. Later, the anticancer activity of the synthesized compounds was screened in vitro against different human cancer cell lines like MCF-7 and A-549, and the results were compared with the standard drug erlotinib. Most of the investigated compounds were found to be active against both cancer cell lines, MCF-7, and A-459. Specifically, compounds 2-(((1-(4-chloro-3,5-dimethoxyphenyl)-1H-1,2,3-triazol-4-yl)methyl)sulfonyl)-5-(1-methyl-1H-indol-3-yl)-1,3,4-oxadiazole and 2-(((1-(3,5-dichlorophenyl)-1H-1,2,3-triazol-4-yl)methyl) sulfonyl)-5-(1-methyl-1H-indol-3-yl)-1,3,4-oxadiazole had superior activity against MCF-7, and remarkable activity against A-549. Similarly, the compound 2-(((1-(3,5-dichlorophenyl)-1H-1,2,3-triazol-4-yl)methyl)sulfonyl)-5-(1-methyl-1H-indol-3-yl)-1,3,4-oxadiazole showed more potent activity against EGFR and compound 2-(((1-(4-chloro-3,5-dimethoxyphenyl)-1H-1,2,3-triazol-4-yl)methyl)sulfonyl)-5-(1-methyl-1H-indol-3-yl)-1,3,4-oxadiazole showed equipotent activity against tyrosine kinase EGFR inhibitory activity.

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This work was supported by regular institutional funding, and no additional grants were obtained.

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Authors and Affiliations

  1. Department of Chemistry, GITAM deemed to be University, Hyderabad Campus, Rudraram, Sangareddy, Hyderabad, 502329, Telangana, India

    Jagan Mohan Reddy Velidandla & Shiva Kumar Koppula

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  1. Jagan Mohan Reddy Velidandla
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  2. Shiva Kumar Koppula
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Author JMRV is research scholar under my supervision who carried out this synthesis and characterization work. Author SKK involved in the supervision of designed chemistry, evaluation of biological activity part, and manuscript writing.

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Correspondence to Shiva Kumar Koppula.

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The data that support the findings of this study are available from the corresponding author upon reasonable request. This article does not contain any studies involving animals or human participants performed by any of the authors. Informed consent was not required for this article. No conflict of interest was declared by the authors.

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Velidandla, J.M.R., Koppula, S.K. Synthesis of Indole-1,3,4-Oxadiazole Based Sulfonyl 1,2,3-Triazoles as Potent Anticancer and EGFR Inhibitors. Russ J Bioorg Chem 49, 1337–1345 (2023). https://doi.org/10.1134/S1068162023060146

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