Literature DB >> 24880489

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

Muhammad Yar1, Marek Bajda2, Lubna Shahzadi3, Sohail Anjum Shahzad4, Maqsood Ahmed5, Muhammad Ashraf6, Umber Alam6, Islam Ullah Khan7, Ather Farooq Khan3.   

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.
Copyright © 2014 Elsevier Inc. All rights reserved.

Entities:  

Keywords:  Acarbose; Biginelli reaction; Dihydropyrimidine; N-acetyl glycine; α-Glucosidase inhibitors

Mesh：

Substances：

Year:  2014        PMID： 24880489     DOI： 10.1016/j.bioorg.2014.05.003

Source DB:  PubMed          Journal:  Bioorg Chem        ISSN： 0045-2068            Impact factor:   5.275


  7 in total

1.  Probing the influence of carboxyalkyl groups on the molecular flexibility and the charge density of apigenin derivatives.

Authors:  Y J Qi; H N Lu; Y M Zhao; N Z Jin
Journal:  J Mol Model       Date:  2017-02-15       Impact factor: 1.810

2.  Inhibition Mechanism of Components Isolated from Morus alba Branches on Diabetes and Diabetic Complications via Experimental and Molecular Docking Analyses.

Authors:  Ryeong-Ha Kwon; Niha Thaku; Binod Timalsina; Se-Eun Park; Jae-Sue Choi; Hyun-Ah Jung
Journal:  Antioxidants (Basel)       Date:  2022-02-14

3.  Crystal structure of ethyl (2S)-9-meth-oxy-2-methyl-4-oxo-3,4,5,6-tetra-hydro-2H- 2,6-methano-benzo[g][1,3,5]oxa-diazocine-11-carboxyl-ate.

Authors:  A Dhandapani; S Manivarman; S Subashchandrabose; B Gunasekaran
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-01-17

4.  Synthesis, Biological Evaluation and Molecular Docking Study of 2-Substituted-4,6-Diarylpyrimidines as α-Glucosidase Inhibitors.

Authors:  Zipeng Gong; Zhenzhen Xie; Jie Qiu; Guangcheng Wang
Journal:  Molecules       Date:  2017-10-30       Impact factor: 4.411

5.  An efficient and targeted synthetic approach towards new highly substituted 6-amino-pyrazolo[1,5-a]pyrimidines with α-glucosidase inhibitory activity.

Authors:  Fariba Peytam; Mehdi Adib; Reihaneh Shourgeshty; Loghman Firoozpour; Mahmoud Rahmanian-Jazi; Mehdi Jahani; Setareh Moghimi; Kouros Divsalar; Mohammad Ali Faramarzi; Somayeh Mojtabavi; Fatemeh Safari; Mohammad Mahdavi; Alireza Foroumadi
Journal:  Sci Rep       Date:  2020-02-13       Impact factor: 4.379

6.  Effects of Hydroxyl Group on the Interaction of Carboxylated Flavonoid Derivatives with S. Cerevisiae α-Glucosidase.

Authors:  Huining Lu; Yanjiao Qi; Yaming Zhao; Nengzhi Jin
Journal:  Curr Comput Aided Drug Des       Date:  2020       Impact factor: 1.606

7.  Design, synthesis, molecular docking, and in vitro α-glucosidase inhibitory activities of novel 3-amino-2,4-diarylbenzo[4,5]imidazo[1,2-a]pyrimidines against yeast and rat α-glucosidase.

Authors:  Fariba Peytam; Ghazaleh Takalloobanafshi; Toktam Saadattalab; Maryam Norouzbahari; Zahra Emamgholipour; Setareh Moghimi; Loghman Firoozpour; Hamid Reza Bijanzadeh; Mohammad Ali Faramarzi; Somayeh Mojtabavi; Parviz Rashidi-Ranjbar; Saeed Karima; Roya Pakraad; Alireza Foroumadi
Journal:  Sci Rep       Date:  2021-06-07       Impact factor: 4.379
  7 in total

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