3-Benzyl(phenethyl)-2-thioxobenzo[g]quinazolines as a new class of potent α-glucosidase inhibitors: Synthesis and molecular docking study

• Published in: Future Medicinal Chemistry
• Main Author: Al-Salahi R.; Ahmad R.; Anouar E.; Iwana Nor Azman N.I.; Marzouk M.; Abuelizz H.A.
• Format: Article
• Language: English
• Published: Future Medicine Ltd. 2018
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85051851796&doi=10.4155%2ffmc-2018-0141&partnerID=40&md5=b8383e3ff482a4404b33b01fafc6d37b
• ISSN: 17568919
• DOI: 10.4155/fmc-2018-0141

Aim: Using a simple modification on a previously reported synthetic route, 3-benzyl(phenethyl)-2-thioxobenzo[g]quinazolin-4(3H)-ones (1 and 2) were synthesized with high yields. Further transformation of 1 and 2 produced derivatives 3-26, which were structurally characterized based on NMR and MS data, and their in vitro α-glucosidase inhibitory activity was evaluated using Baker's yeast α-glucosidase enzyme. Results: Compounds 2, 4, 8, 12 and 20 exhibited the highest activity (IC 50 = 69.20, 59.60, 49.40, 50.20 and 83.20 μM, respectively) compared with the standard acarbose (IC 50 = 143.54 μM). Conclusion: 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. © 2018 2018 Newlands Press.