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用于α-葡萄糖苷酶抑制以治疗2型糖尿病的新型二氢嘧啶合成：体外生物学评价和计算机模拟对接

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

作者信息

Yar Muhammad, Bajda Marek, Shahzadi Lubna, Shahzad Sohail Anjum, Ahmed Maqsood, Ashraf Muhammad, Alam Umber, Khan Islam Ullah, Khan Ather Farooq

机构信息

Interdisciplinary Research Center in Biomedical Materials, COMSATS Institute of Information Technology, Lahore 54000, Pakistan.

Faculty of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland; Department of Physicochemical Drug Analysis, Faculty of Pharmacy, Jagiellonian University Medical College, Medyczna 9, 30-688 Cracow, Poland.

出版信息

Bioorg Chem. 2014 Jun;54:96-104. doi: 10.1016/j.bioorg.2014.05.003. Epub 2014 May 15.

DOI:10.1016/j.bioorg.2014.05.003
PMID:24880489
Abstract

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 α-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 μM), to show the enzyme - inhibitor interactions.

摘要

通过廉价且无毒的N-乙酰甘氨酸（NAG）催化芳香醛与乙酰乙酸乙酯和尿素/硫脲的反应，建立了一种便捷高效的二氢嘧啶合成新方法。该方法适用于各种取代醛以及尿素和硫脲。它还被用于合成双环氧桥嘧啶衍生物（4d，4j）。生物活性测定表明，所合成的大多数化合物在低微摩尔浓度下对α-葡萄糖苷酶表现出适度的抑制活性。还对活性最高的化合物4f（IC50值为112.21±0.97μM）进行了分子对接研究，以展示酶与抑制剂的相互作用。

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