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
收藏
页码：96 / 104
页数：9
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