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Design, Synthesis and in Vitro Α-Glucosidase Inhibition of Novel Dihydropyrano[3,2-C]Quinoline Derivatives As Potential Anti-Diabetic Agents Publisher Pubmed



Nikookar H1 ; Mohammadikhanaposhtani M2 ; Imanparast S3 ; Faramarzi MA3 ; Ranjbar PR1 ; Mahdavi M4 ; Larijani B4
Authors
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Authors Affiliations
  1. 1. School of Chemistry, College of Science, University of Tehran, Tehran, Iran
  2. 2. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
  3. 3. Department of Pharmaceutical Biotechnology, Faculty of Pharmacy and Biotechnology Research Center, Tehran University of Medical Sciences, Iran
  4. 4. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: Bioorganic Chemistry Published:2018


Abstract

A novel series of dihydropyrano[3,2-c]quinoline derivatives 6a–q were synthesized and evaluated for their in vitro α-glucosidase inhibitory activities. All newly synthesized compounds displayed potent α-glucosidase inhibitory activity in the range of 10.3 ± 0.3 µM–172.5 ± 0.8 µM against the yeast α-glucosidase enzyme when compared to the standard drug acarbose (IC50 = 750.0 ± 1.5 µM). Among these compounds, compounds 6e and 6d displayed the most potent α-glucosidase inhibitory activity (IC50 = 10.3 ± 0.3 and 15.7 ± 0.5 µM, respectively). The kinetic analysis of the most potent compounds 6e and 6d revealed that compound 6e inhibited α-glucosidase in an uncompetitive manner (Ki = 11 µM) while compound 6d was a non-competitive inhibitor (Ki = 28 µM) of the enzyme. Then, the cytotoxicity of the most potent compounds (i.e., compounds 6a, 6d, 6e, 6 g, 6j, and 6l) were evaluated for toxicity using the breast cancer cell lines MDA-MB231, MCF-7, and T-47D by using a MTT assay, and no toxicity was observed. © 2018
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