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

Autor: Syed Ahmad Tirmizi, A. Hazeeq, Hapipah Mohd Ali, R. H. Ahmad, Muhammad Suhail Sharif, A. M. Alnajeebi, Shahad W. Kattan, A. Raheel, W. Alelwani, M. B. Taj, Abbas, N. A. Babteen
Rok vydání: 2019
Předmět:
Zdroj: Russian Journal of Organic Chemistry. 55:1047-1052
ISSN: 1608-3393
1070-4280
DOI: 10.1134/s1070428019070224
Popis: 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.
Databáze: OpenAIRE