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

被引：30

作者：

Al-Salahi, Rashad ^{[1
]}

Ahmad, Rohaya ^{[2
]}

Anouar, ElHassane ^{[3
]}

Azman, Nor Izzati Iwana Nor ^{[2
]}

Marzouk, Mohamed ^{[3
,4
]}

Abuelizz, Hatem A. ^{[1
]}

机构：

[1] King Saud Univ, Coll Pharm, Dept Pharmaceut Chem, POB 2457, Riyadh 11451, Saudi Arabia

[2] Univ Teknol MARA, Fac Sci Appl, Shah Alam 40450, Selangor Darul, Malaysia

[3] Prince Sattam bin Abdulaziz Univ, Dept Chem, Coll Sci & Humanities, POB 83, Al Kharj 11942, Saudi Arabia

[4] Natl Res Ctr, Chem Nat Prod Grp, Ctr Excellence Adv Sci, Cairo 12622, Egypt

来源：

FUTURE MEDICINAL CHEMISTRY | 2018年 / 10卷 / 16期

关键词：

alpha-glucosidase; antidiabetic; benzoquinazoline; molecular docking; BIOLOGICAL EVALUATION; QUINAZOLIN-4(3H)-ONE DERIVATIVES;

D O I：

10.4155/fmc-2018-0141

中图分类号：

R914 [药物化学];

学科分类号：

100705 [微生物与生化药学];

摘要：

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 alpha-glucosidase inhibitory activity was evaluated using Baker's yeast alpha-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 mu M, respectively) compared with the standard acarbose (IC50 = 143.54 mu M). Conclusion: A new class of potent alpha-glucosidase inhibitors was identified, and the molecular docking predicted plausible binding interaction of the targets in the binding pocket of alpha-glucosidase and rationalized the structure-activity relationship (SARs) of the target compounds.

引用

页码：1889 / 1905

页数：17

共 30 条

[1]

In vitro evaluation of new 2-phenoxy-benzo [g][1,2,4]triazolo[1,5-a] quinazoline derivatives as antimicrobial agents [J].