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

Taj, M.B. and Raheel, A. and Alelwani, W. and Babteen, N. and Kattan, S. and Alnajeebi, A. and Sharif, M. and Ahmad, R.H. and Abbas, - and Hazeeq, A. and Tirmizi, S.A. and Ali, Hapipah Mohd (2019) One-Pot CuO-Catalyzed Green Synthesis of N(N′)-Arylbenzamidines as Potential Enzyme Inhibitors. Russian Journal of Organic Chemistry, 55 (7). pp. 1047-1052. ISSN 1070-4280, DOI https://doi.org/10.1134/S1070428019070224.

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Official URL: https://doi.org/10.1134/S1070428019070224

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. © 2019, Pleiades Publishing, Ltd.

Item Type: Article
Funders: UNSPECIFIED
Uncontrolled Keywords: acetylcholinesterase; lipoxygenase; N-substituted benzamidines; reverse transcriptase; α-glucosidase
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Divisions: Faculty of Science > Department of Chemistry
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 08 Jan 2020 05:53
Last Modified: 08 Jan 2020 05:53
URI: http://eprints.um.edu.my/id/eprint/23341

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