Abstract
We report herein the synthesis antioxidant and Aβ anti-aggregation capacity of (E)-N-benzyl-N-[2-(benzylamino)-2-oxoethyl]-3-(aryl)acrylamides and related (R)-N-benzyl-N-(2-(benzylamino)-2-oxoethyl)-5-(1,2-dithiolan-3-yl)pentanamides 1-12. These compounds have been obtained, via Ugi four-component reaction, from modest to good yields. Their antioxidant analysis, using the DPPH and ORAC assays, allowed us to identify compounds 8 and 9, as potent antioxidant agents, showing also strong Aβ1-40 self-aggregation inhibition, two biological properties of interest in pathologies linked to the oxidative stress, such as Alzheimer's disease.
Keywords:
(R)-Lipoic acid; Antioxidants; Aβ(1−40) self-aggregation inhibition; Benzyl isocyanide; Benzylamine; Caffeic acid; Ferulic acid; Multicomponent reactions; Ugi four-component reaction.
Copyright © 2018 Elsevier Inc. All rights reserved.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Amyloid beta-Peptides / metabolism
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Caffeic Acids / chemical synthesis
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Caffeic Acids / chemistry
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Caffeic Acids / pharmacology*
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Cell Line, Tumor
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Coumaric Acids / chemical synthesis
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Coumaric Acids / chemistry
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Coumaric Acids / pharmacology*
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Free Radical Scavengers / chemical synthesis
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Free Radical Scavengers / chemistry
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Free Radical Scavengers / pharmacology*
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Humans
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Hydrogen Peroxide / pharmacology
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Molecular Structure
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Neuroprotective Agents / chemical synthesis
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Neuroprotective Agents / chemistry
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Neuroprotective Agents / pharmacology
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Oxidative Stress / drug effects
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Peptide Fragments / metabolism
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Protein Multimerization / drug effects*
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Structure-Activity Relationship
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Thioctic Acid / analogs & derivatives*
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Thioctic Acid / chemical synthesis
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Thioctic Acid / chemistry
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Thioctic Acid / pharmacology*
Substances
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Amyloid beta-Peptides
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Caffeic Acids
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Coumaric Acids
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Free Radical Scavengers
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Neuroprotective Agents
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Peptide Fragments
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amyloid beta-protein (1-40)
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Thioctic Acid
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ferulic acid
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Hydrogen Peroxide