3-Benzyl(phenethyl)-2-thioxobenzo

• Published in: Future medicinal chemistry Vol. 10; no. 16; pp. 1889 - 1905
• Main Authors: Al-Salahi, Rashad, Ahmad, Rohaya, Anouar, ElHassane, Iwana Nor Azman, Nor Izzati, Marzouk, Mohamed, Abuelizz, Hatem A
• Format: Journal Article
• Language: English
• Published: Future Science Ltd 01.06.2018; 01.08.2018
• Subjects: antidiabetic; benzoquinazoline; molecular docking; α-glucosidase
• ISSN: 1756-8919; 1756-8927
• DOI: 10.4155/fmc-2018-0141

Using a simple modification on a previously reported synthetic route, 3-benzyl(phenethyl)-2-thioxobenzo[ ]quinazolin-4(3 )-ones ( and ) were synthesized with high yields. Further transformation of and produced derivatives - , which were structurally characterized based on NMR and MS data, and their α-glucosidase inhibitory activity was evaluated using Baker's yeast α-glucosidase enzyme. Compounds , , , and exhibited the highest activity (IC = 69.20, 59.60, 49.40, 50.20 and 83.20 μM, respectively) compared with the standard acarbose (IC = 143.54 μM). A new class of potent α-glucosidase inhibitors was identified, and the molecular docking predicted plausible binding interaction of the targets in the binding pocket of α-glucosidase and rationalized the structure-activity relationship (SARs) of the target compounds.