Novel synthesis of dihydropyrimidines for α-glucosidase inhibition to treat type 2 diabetes: In vitro biological evaluation and in silico docking

被引：55

作者：

Yar, Muhammad ^{[1
]}

Bajda, Marek ^{[2
,3
]}

Shahzadi, Lubna ^{[1
]}

Shahzad, Sohail Anjum ^{[4
]}

Ahmed, Maqsood ^{[5
]}

Ashraf, Muhammad ^{[6
]}

Alam, Umber ^{[6
]}

Khan, Islam Ullah ^{[7
]}

Khan, Ather Farooq ^{[1
]}

机构：

[1] COMSATS Inst Informat Technol, Interdisciplinary Res Ctr Biomed Mat, Lahore 54000, Pakistan

[2] Univ Warsaw, Fac Chem, PL-02093 Warsaw, Poland

[3] Jagiellonian Univ, Dept Physicochem Drug Anal, Fac Pharm, Coll Med, PL-30688 Krakow, Poland

[4] COMSATS Inst Informat Technol, Dept Chem, Abbottabad 22060, Pakistan

[5] Islamia Univ Bahawalpur, Dept Chem, Bahawalpur 63100, Pakistan

[6] Islamia Univ Bahawalpur, Dept Biochem & Biotechnol, Bahawalpur 63100, Pakistan

[7] Govt Coll Univ, Dept Chem, Lahore 54000, Pakistan

来源：

BIOORGANIC CHEMISTRY | 2014年 / 54卷

关键词：

alpha-Glucosidase inhibitors; Dihydropyrimidine; Biginelli reaction; N-acetyl glycine; Acarbose; ONE-POT SYNTHESIS; SOLVENT-FREE CONDITIONS; BIGINELLI REACTION; EFFICIENT SYNTHESIS; ULTRASOUND IRRADIATION; 3,4-DIHYDROPYRIMIDIN-2(1H)-ONES; DERIVATIVES; MONASTROL; CATALYST; CHLORIDE;

D O I：

10.1016/j.bioorg.2014.05.003

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A convenient and efficient new method has been established for the synthesis of dihydropyrimidines by inexpensive and non-toxic N-acetyl glycine (NAG) catalysed reaction of aromatic aldehydes with ethyl acetoacetate and urea/thiourea. This method is applicable for various substituted aldehydes as well as urea and thiourea. It has also been used to synthesize bicyclic oxygen-bridged pyrimidine derivatives (4d, 4j). The biological assay revealed that the majority of compounds synthesized displayed modest inhibitory activity against alpha-glucosidase at low micro-molar concentrations. Molecular docking studies were also performed on the most active compound, 4f (with IC50 value 112.21 +/- 0.97 mu M), to show the enzyme - inhibitor interactions. (C) 2014 Elsevier Inc. All rights reserved.

引用

页码：96 / 104

页数：9

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