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

Al-Salahi R 1 , Ahmad R 2 , Anouar E 3 , Iwana Nor Azman NI 2 , Marzouk M 3 , Abuelizz HA 1

Affiliations 

  • 1 Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO box 2457, Riyadh 11451, Saudi Arabia
  • 2 Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 shah Alam, Selangor Darul Ehsan, Malaysia
  • 3 Department of Chemistry, College of Science & Humanities, Prince Sattam bin Abdulaziz University, PO Box 83, Al Kharj 11942, Saudi Arabia
Future Med Chem, 2018 08 01;10(16):1889-1905.
PMID: 29882426 DOI: 10.4155/fmc-2018-0141

Abstract

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 (IC50 = 69.20, 59.60, 49.40, 50.20 and 83.20 μM, respectively) compared with the standard acarbose (IC50 = 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.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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