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One-Pot CuO-Catalyzed Green Synthesis of N(N′)-Arylbenzamidines as Potential Enzyme Inhibitors

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Abstract

Ten N(N′)-arylbenzamidines were synthesized in 60–77% yield by one-pot microwave-assisted reaction of the corresponding N-arylbenzamides with aniline or ammonia in the presence of copper(II) oxide powder. The synthesized compounds were evaluated in vitro for inhibitory activity against several enzymes, namely acetylcholinesterase, butyrylcholinesterase, lipoxygenase, α-glucosidase, urease, and reverse transcriptase. Some compounds showed very good acetylcholinesterase and butyrylcholinesterase inhibitory activity. N′-(1,3-Benzothiazol-2-yl)- and N′-(1,3,4-thiadiazol-2-yl)benzamidines were the most active α-glucosidase inhibitors with IC50 values of 134.2 and 244.57 µM, respectively. N′-(1,3-Benzothiazol-2-yl)benzamidine also inhibited urease. Most of the obtained compounds showed inhibitory activity against reverse transcriptase (anti-HIV activity), presumably due to intermolecular hydrogen bonding, good solubility, and hydrophilicity.

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Authors and Affiliations

  1. Department of Chemistry, Quaid-e-Azam University, Islamabad, Pakistan

    M. B. Taj, A. Raheel & S. A. Tirmizi

  2. Department of Chemistry, Islamia University, Bahawalpur, Pakistan

    M. B. Taj & M. Sharif

  3. Department of Chemistry, University of Malaya, Kuala Lampur, Malaysia

    M. B. Taj,  Abbas, A. Hazeeq & H. B. M. Ali

  4. Department of Biochemistry, Faculty of Science, University of Jeddah, Jeddah, Saudi Arabia

    W. Alelwani & N. Babteen

  5. College of Applied Medical Sciences, Taibah University, Yanbu, Saudi Arabia

    S. Kattan & A. Alnajeebi

  6. Department of Nano Science and Technology, National Centre for Physics, Islamabad, Pakistan

    R. H. Ahmad

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  1. M. B. Taj
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  2. A. Raheel
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Correspondence to M. B. Taj.

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Taj, M.B., Raheel, A., Alelwani, W. et al. One-Pot CuO-Catalyzed Green Synthesis of N(N′)-Arylbenzamidines as Potential Enzyme Inhibitors. Russ J Org Chem 55, 1047–1052 (2019). https://doi.org/10.1134/S1070428019070224

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  • DOI: https://doi.org/10.1134/S1070428019070224

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