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Synthesis, Identification, Antibacterial Activity, ADME/T and 1BNA-Docking Investigations of 8-Quinolinol Analogs Bearing a Benzimidazole Moiety

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Abstract

Given the pharmacological significance of 8-quinolinols and benzimidazoles, in the present paper, two series of new N-Heterocyclic having 8-quinolinol and benzimidazole moieties within a single molecular framework were prepared and characterized by elemental analysis, IR, and 13C/1H NMR techniques. To evaluate the desired compound as DNA-binder 3a, 3d, 7a, and 7d were docked with 1BNA DNA using AutoDock version 4.2. On the other hand, many proteins that are crystal structure of the BRCT repeat region from the breast cancer-associated protein, BRCA1 (ID: 1JNX), structure of a b-DNA dodecamer (ID: 1BNA), crystal structure of VEGFR kinase (liver cancer) protein (ID: 3WZE), and crystal structure of an allosteric Eya2 phosphatase inhibitor (lung cancer) protein versus (ID: 5ZMA) proteins, were used to compare the biological activities of all molecules using Maestro Molecular modeling platform. Afterward, ADME/T analysis of the molecules was performed. The derivatives of two series and Nitroxoline drugs were assessed for in vitro antibacterial activity against four microorganisms, including, two gram +bacteria such as B. subtilis, S. aureus, and two gram −bacteria such as E. ludwigii, E. coli. All derivatives were found to have moderate to good antibacterial potential. Of the 9 derivatives, 7d has significant antibacterial potential with MIC values of below 20 μg/mL comparable to Nitroxoline vs. all bacteria.

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Authors and Affiliations

  1. Laboratory of Organic Chemistry, Catalysis, and Environment, Department of Chemistry, Faculty of Sciences, Ibn Tofaïl University, PO Box 133, 14000, Kenitra, Morocco

    M. El Faydy & B. Lakhrissi

  2. Laboratory of Nutrition, Health, and Environment, Department of Biology, Faculty of Sciences, Ibn Tofaïl University, PO Box 133, 14000, Kenitra, Morocco

    N. Dahaieh & K. Ounine

  3. Department of Chemistry and Earth Sciences, Qatar University, PO Box 2713, Doha, Qatar

    I. Warad

  4. Department of Chemistry, Faculty of Science, Sivas Cumhuriyet University, 58140, Sivas, Turkey

    B. Tüzün

  5. Laboratory of Materials, Nanotechnology, and Environment, Department of Chemistry, Faculty of Sciences, Mohammed V University in Rabat, Av. Ibn Battouta, PO Box 1014, Agdal-Rabat, Morocco

    A. Zarrouk

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  1. M. El Faydy
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El Faydy, M., Dahaieh, N., Ounine, K. et al. Synthesis, Identification, Antibacterial Activity, ADME/T and 1BNA-Docking Investigations of 8-Quinolinol Analogs Bearing a Benzimidazole Moiety. Arab J Sci Eng 47, 497–510 (2022). https://doi.org/10.1007/s13369-021-05749-7

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