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Current Organic Chemistry

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ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

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Research Article

2,4-Dioxochroman Moiety Linked to 1,2,3-triazole Derivatives as Novel α-glucosidase Inhibitors: Synthesis, In vitro Biological Evaluation, and Docking Study

Author(s): Marjan Mollazadeh, Maryam Mohammadi-Khanaposhtani, Yousef Valizadeh, Afsaneh Zonouzi, Mohammad Ali Faramarzi, Parsa Hariri, Mahmood Biglar, Bagher Larijani, Haleh Hamedifar, Mohammad Mahdavi* and Nima Sepehri*

Volume 24, Issue 17, 2020

Page: [2019 - 2027] Pages: 9

DOI: 10.2174/1385272824999200802181634

Price: $65

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.

Keywords: 2, 4-Dioxochroman, 1, 2, 3-Triazole, In vitro evaluation, α-Glucosidase, In silico docking study, Diabetes.

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