Synthesis, crystal structure, biological evaluation, docking study, and DFT calculations of 1-amidoalkyl-2-naphthol derivative

摘要

An eco-friendly and efficient synthesis of N-((2,4-dichlorophenyl)(2-hydroxynaphthalen-1-yl)methyl) acrylamide (NDHA), using phenylboronic acid as catalyst, has been reported. NDHA was fully characterized by various physical and spectroscopic techniques, and the proposed structure was confirmed by single-crystal X-ray analysis. In vitro antioxidant activity has been carried out using DPPH, ABTS, Ferricphenanthroline and CUPRAC assays, and it was found that NDHA is a potent antioxidant agent. This result has been confirmed by DFT calculations. The inhibitory potential of the synthesized compound on cholinesterase and alpha-glucosidase enzymes was also investigated. The results showed that NDHA is a promising AChE and alpha-glucosidase inhibitor. Binding modes between the (R) and (S) enantiomers of NDHA and the target enzymes were determined using docking studies. (C) 2020 Elsevier B.V. All rights reserved.