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Potent α-amylase inhibitors and radical (DPPH and ABTS) scavengers based on benzofuran-2-yl(phenyl)methanone derivatives: Syntheses, in vitro, kinetics, and in silico studies.
- Source :
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Bioorganic chemistry [Bioorg Chem] 2020 Nov; Vol. 104, pp. 104238. Date of Electronic Publication: 2020 Aug 28. - Publication Year :
- 2020
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Abstract
- Thirty benzofuran-2-yl(phenyl)methanones 1-30 were synthesized and characterized their structures by spectroscopic techniques. Substituted phenacyl bromide and different derivatives of 2-hydroxy-benzaldehyde treated in the presence of anhydrous K <subscript>2</subscript> CO <subscript>3</subscript> in acetonitrile at room temperature to afford the desired benzofurans 1-30. All compounds were screened for their in vitro α-amylase inhibitory and radical scavenging (DPPH and ABTS) activities. Results revealed that para substituted compounds were found to be more active than the others with IC <subscript>50</subscript> values ranges for α-amylase inhibition (IC <subscript>50</subscript>  = 18.04-48.33 µM), DPPH (IC <subscript>50</subscript>  = 16.04-32.33 µM) and ABTS (IC <subscript>50</subscript>  = 16.99-33.01 µM) radical scavenging activities. Activities results were compared with the standards acarbose (IC <subscript>50</subscript>  = 16.08 ± 0.07 µM) for α-amylase, ascorbic acid (IC <subscript>50</subscript>  = 15.08 ± 0.03 and 15.09 ± 0.17 µM) for DPPH and ABTS radical scavenging activities, respectively. Kinetic studies predicted that all compounds followed non-competitive mechanism of inhibition. Molecular docking results showed good protein-ligand interactions profile against the corresponding target. To the best of our knowledge, out of thirty molecules, ten compounds 18-20, 22, and 25-30 were structurally new.<br /> (Copyright © 2020 Elsevier Inc. All rights reserved.)
- Subjects :
- Benzofurans chemical synthesis
Benzofurans chemistry
Benzothiazoles antagonists & inhibitors
Biphenyl Compounds antagonists & inhibitors
Dose-Response Relationship, Drug
Enzyme Inhibitors chemical synthesis
Enzyme Inhibitors chemistry
Free Radical Scavengers chemical synthesis
Free Radical Scavengers chemistry
Kinetics
Molecular Structure
Picrates antagonists & inhibitors
Structure-Activity Relationship
Sulfonic Acids antagonists & inhibitors
alpha-Amylases metabolism
Benzofurans pharmacology
Enzyme Inhibitors pharmacology
Free Radical Scavengers pharmacology
Molecular Docking Simulation
alpha-Amylases antagonists & inhibitors
Subjects
Details
- Language :
- English
- ISSN :
- 1090-2120
- Volume :
- 104
- Database :
- MEDLINE
- Journal :
- Bioorganic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 32911195
- Full Text :
- https://doi.org/10.1016/j.bioorg.2020.104238