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Green synthesis of diethyl((2-iodo-4-(trifluoromethyl)phenyl)amino)(aryl)methyl)phosphonates as potent α-glucosidase inhibitors

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Abstract Novel diethyl((2-iodo-4-(trifluoromethyl)phenyl)amino)(aryl)methyl)phosphonates (4a-j) were synthesized via a simple and efficient one pot by three-component condensation reaction (Kabachnik-Fields reaction) of 2-iodo-4-trifluoromethyl aniline, aromatic aldehydes and diethyl phosphite in presence of… Click to show full abstract

Abstract Novel diethyl((2-iodo-4-(trifluoromethyl)phenyl)amino)(aryl)methyl)phosphonates (4a-j) were synthesized via a simple and efficient one pot by three-component condensation reaction (Kabachnik-Fields reaction) of 2-iodo-4-trifluoromethyl aniline, aromatic aldehydes and diethyl phosphite in presence of anatase TiO2 nanoparticles as catalyst under solvent free conditions. The molecular docking studies of synthesized compounds with α-glucosidase enzyme revealed that these compounds have strong α-glucosidase inhibitory activity. The synthesized compounds (4a-j) are also screened for in vitro α-glucosidase inhibitory activity and the results showed compound 4i as the strongest inhibitor and compounds 4a, 4b, 4f and 4g as stronger inhibitors even better than the reference standard acarbose. Graphical Abstract

Keywords: diethyl iodo; iodo trifluoromethyl; phenyl amino; iodo; trifluoromethyl phenyl

Journal Title: Synthetic Communications
Year Published: 2020

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