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2,4-Dioxochroman Moiety Linked to 1,2,3-Triazole Derivatives As Novel Α-Glucosidase Inhibitors: Synthesis, in Vitro Biological Evaluation, and Docking Study Publisher



Mollazadeh M1 ; Mohammadikhanaposhtani M2 ; Valizadeh Y3 ; Zonouzi A1 ; Faramarzi MA4 ; Hariri P4 ; Biglar M3 ; Larijani B3 ; Hamedifar H5 ; Mahdavi M3 ; Sepehri N6
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Source: Current Organic Chemistry Published:2020


Abstract

In this study, a novel series of 2,4-dioxochroman-1,2,3-triazole hybrids 8a-l was synthesized by click reaction. These compounds were screened against α-glucosidase through in vitro and in silico evaluations. All the synthesized hybrids exhibited excellent α-glucosidase inhibition in comparison to standard drug acarbose. Representatively, 3-((((1-(3,4-dichlorobenzyl)-1H-1,2,3-triazol-4-yl)methyl)amino)methylene)chroman-2,4-dione 8h with IC50 = 20.1 ± 1.5 µM against α-glucosidase, was 37-times more potent than acarbose. Enzyme kinetic study revealed that compound 8h was a competitive inhibitor against α-glucosidase. In silico docking study on chloro derivatives 8h, 8g, and 8i were also performed in the active site of α-glucosidase. Evaluations on obtained interaction modes and binding energies of these compounds confirmed the results obtained through in vitro α-glucosidase inhibition. © 2020 Bentham Science Publishers.
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