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Synthesis, cytotoxicity, and docking study of novel 1-naphthyl-5-aryl-1H-1,2,4-triazole-3-carboxamides

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Abstract

A new series of 1-naphthyl-5-aryl-1H-1,2,4-triazole-3-carboxamide derivatives were synthesized and structurally proved by 1H and 13C NMR along with high-resolution mass spectrometry. The cytotoxic activity of the newly synthesized compounds was evaluated. Compounds showed a pronounced inhibitory effect against cellular localization of tubulin. Flow cytometric analysis showed that Hep-G2 cells treated indicated a predominated growth arrest at the G2/M-phase compared to that of S-phase. Molecular modeling study using MOE program indicated that most of the target compounds showed good binding with the colchicine-binding site of β-subunit of tubulin with the binding free energy (∆G) values of about 42 kJ/mol.

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Acknowledgements

This work was financially supported by the Science and Technology Development Fund (STDF) of Egypt (Project No. 2943 Basic and Applied Research). Moreover, all eternal thanks to the National Cancer Institute (NCI), Bethesda, Maryland, USA, for performing the anticancer testing of the target compounds over 60 cancer cell lines. Finally, we would like to thank Prof. Amira M. Gamal-Eldeen, Cancer Biology Laboratory, Center of Excellence for Advanced Sciences, National Research Center, Cairo, Egypt, for her help in studying the cytotoxicity of the synthesized compounds.

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Authors and Affiliations

  1. Faculty of Pharmacy, Organic Chemistry Department, Port Said University, Port Said, Egypt

    Islam Zaki

  2. Faculty of Pharmacy, Organic Chemistry Department, Al-Azhar University, Assuit, Egypt

    Mohamed Ramadan & Mostafa H. Abdelrahman

  3. Faculty of Pharmacy, Medicinal Chemistry Department, Minia University, Minia, Egypt

    Omar M. Aly

  4. College of Clinical Pharmacy, Pharmaceutical Chemistry Department, AlBaha University, AlBaha, Saudi Arabia

    Omar M. Aly

Authors
  1. Islam Zaki
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  2. Mohamed Ramadan
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  3. Mostafa H. Abdelrahman
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  4. Omar M. Aly
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Corresponding author

Correspondence to Mohamed Ramadan.

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Zaki, I., Ramadan, M., Abdelrahman, M.H. et al. Synthesis, cytotoxicity, and docking study of novel 1-naphthyl-5-aryl-1H-1,2,4-triazole-3-carboxamides. Monatsh Chem 148, 1483–1496 (2017). https://doi.org/10.1007/s00706-016-1910-8

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  • DOI: https://doi.org/10.1007/s00706-016-1910-8

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