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Design, Synthesis and in Vitro Α-Glucosidase Inhibition of Novel Coumarin-Pyridines As Potent Antidiabetic Agents Publisher



Adib M1 ; Peytam F1 ; Rahmanianjazi M1 ; Mohammadikhanaposhtani M2 ; Mahernia S3, 4 ; Bijanzadeh HR5 ; Jahani M1 ; Imanparast S6 ; Faramarzi MA6 ; Mahdavi M7 ; Larijani B7
Authors

Source: New Journal of Chemistry Published:2018


Abstract

In this work, we report an efficient, one-pot and three-component synthesis of novel coumarin fused pyridine derivatives 4a-p. Heating the mixture of 4-hydroxycoumarins and ammonium acetate in DMF gave the corresponding 4-aminocoumarins, which subsequently went through Michael addition-cyclocondensation with α-azidochalcone derivatives to produce our desired products in high yields. The synthesized compounds 4a-p were evaluated for α-glucosidase inhibitory activity and all of them exhibited excellent in vitro yeast α-glucosidase inhibition with IC50 values ranging from 101.0 ± 2.0 to 227.3 ± 1.4 μM when compared with the standard drug acarbose (IC50 = 750.0 ± 1.5 μM). A kinetic study of the most potent compound 4i revealed that it inhibited α-glucosidase in a competitive mode. A docking study of the most active compounds 4i, 4h, and 4j was also performed. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
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