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Synthesis of Benzothiazole/Benzimidazole-Conjugated Imidazoles as Anticancer Agents and Their Molecular Modeling

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Abstract

An efficient and high-yielding method was developed for the synthesis of N-(benzo[d]thiazol-2-yl)-6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carboxamide derivatives by reacting benzo[d]thiazol-2-amine/1H-benzo[d]imidazol-2-amine with 5-bromo-6-methoxypicolinic acid in the presence of HBTU/Et3N in DMSO followed by coupling with 4-methyl-1H-imidazole in the presence of K2CO3/CuI in trans-1,2-diaminocyclohexane.The mild reaction conditions and easy operations allow introducing a wide range of functionalities, as well as a high reaction efficiency. The synthesized compounds were tested for their anticancer potential against MCF-7 and DU145 human cancer cell lines. N-(5-Fluoro-1H-benzo[d]imidazol-2-yl)- and N-(4-fluorobenzo[d]thiazol-2-yl)-6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridine-2-carboxamides exhibited the highest activity among the test compounds against both the cell lines, with IC50 values ranging from 8.9 to 10.8 µM. Docking analysis revealed the potential inhibitory activity of the former compound against VEGFR-2 kinase, with the binding energy of 7.9 kcal/mol.

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ACKNOWLEDGMENTS

The authors are grateful to the authorities of DST-PURSE, Department of Chemistry, Osmania University, Hyderabad, Telangana, and CSIR for providing funds and fellowship support.

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Authors and Affiliations

  1. Osmania University, Department of Chemistry, 500007, Hyderabad, India

    Kurapati Ravi, Bala Narsimha Dhoddi, Jalapathi Pochampally & Raghavender Matta

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  1. Kurapati Ravi
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  2. Bala Narsimha Dhoddi
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  3. Jalapathi Pochampally
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  4. Raghavender Matta
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Correspondence to Jalapathi Pochampally.

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Ravi, K., Dhoddi, B.N., Pochampally, J. et al. Synthesis of Benzothiazole/Benzimidazole-Conjugated Imidazoles as Anticancer Agents and Their Molecular Modeling. Russ J Org Chem 59, 915–923 (2023). https://doi.org/10.1134/S1070428023050226

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