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Discovery of Phthalimide-1,2,3-Triazole-N-Phenylacetamide Hybrids As Potent Α-Glucosidase Inhibitors: Design, Synthesis, Admet Prediction, and in Vitro and in Silico Enzymatic Evaluations Publisher



Gavanrudi MR1 ; Halimi M2 ; Najafzadehvarzi H3 ; Alikhani M4 ; Moazzam A5 ; Farzipour S6 ; Hosseini S7 ; Mojtabavi S8 ; Faramarzi MA8 ; Nasliesfahani E9 ; Mohammadikhanaposhtani M3 ; Mahdavi M5
Authors

Source: ChemistrySelect Published:2023


Abstract

Thirteen new derivatives of the phthalimide-1,2,3-triazole-N-phenylacetamide hybrids were synthesized via simple chemical reactions. These hybrids were evaluated for their inhibitory potential against α-glucosidase in vitro and in silico. Among these thirteen derivatives, seven compounds showed excellent inhibition against studied enzyme (IC50 values=1.30−31.7 μM) as compared to positive control acarbose (IC50 value=750.1 μM) and among them, compound with 2,4-dichloro substituent on the phenyl ring of N-phenylacetamide moiety was identified as the most potent inhibitor against α-glucosidase. This compound was almost 577-fold more active than acarbose. Kinetic study on the most potent compound demonstrated that this compound is a competitive α-glucosidase inhibitor. To understand the interaction mode, stability, and flexibility of the most potent compounds, molecular docking and molecular dynamics studies were conducted. Furthermore, the drug-likeness, pharmacokinetic, and toxicity properties of the title compounds were predicted by in silico studies. © 2023 Wiley-VCH GmbH.
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