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

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 si...

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Veröffentlicht in:Journal of molecular structure 2020-07, Vol.1212, p.128179, Article 128179
Hauptverfasser: Boudebbous, Khawla, Boulebd, Houssem, Boulcina, Raouf, Bendjeddou, Lamia, Bensouici, Chawki, Merazig, Hocine, Debache, Abdelmadjid
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Sprache:eng
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Zusammenfassung: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, Ferric-phenanthroline 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 α-glucosidase enzymes was also investigated. The results showed that NDHA is a promising AChE and α-glucosidase inhibitor. Binding modes between the (R) and (S) enantiomers of NDHA and the target enzymes were determined using docking studies. [Display omitted] •Eco-friendly and efficient synthesis of 1-amidoalkyl-2-naphthol derivative (NDHA) has been reported.•Molecular structure of NDHA was full characterized by physical and spectroscopic techniques, and confirmed by X-ray analysis.•Antioxidant, anti-cholinesterase and α-glucosidase inhibitory activities have been studied.•In silico studies including DFT calculations and molecular modeling have been investigated.
ISSN:0022-2860
1872-8014
DOI:10.1016/j.molstruc.2020.128179