Design and Evaluation of 4-Aminophenol and Salicylate Derivatives as Free-Radical Scavenger

This theoretical and experimental study describes the design and evaluation of the free‐radical scavenging effect for the molecular association of 4‐aminophenol and salicylate derivatives. For this purpose, we employed theoretical methods for the selection of antioxidant drugs and the rapid methods...

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Bibliographic Details
Published in:Chemical biology & drug design 2013-03, Vol.81 (3), p.414-419
Main Authors: Borges, Rosivaldo S., Pereira, Glaécia A. N., Vale, Joyce K. L., França, Luiz C. S., Monteiro, Marta C., Alves, Cláudio N., da Silva, Albérico B. F.
Format: Article
Language:English
Subjects:
1,1‐diphenyl‐2‐picrylhydrazyl radical
1-diphenyl-2-picrylhydrazyl radical
Aminophenols - chemical synthesis
Aminophenols - chemistry
Aminophenols - pharmacology
antioxidants
Computer-Aided Design
density functional theory
design
Drug Design
Drug Evaluation, Preclinical
Erythrocytes - drug effects
Erythrocytes - metabolism
Free Radical Scavengers - chemical synthesis
Free Radical Scavengers - chemistry
Free Radical Scavengers - pharmacology
Humans
Lipid Peroxidation - drug effects
non-steroidal anti-inflammatory drugs
Quantum Theory
Salicylates - chemical synthesis
Salicylates - chemistry
Salicylates - pharmacology
Structure-Activity Relationship
thiobarbituric acid reactive substances
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Summary:This theoretical and experimental study describes the design and evaluation of the free‐radical scavenging effect for the molecular association of 4‐aminophenol and salicylate derivatives. For this purpose, we employed theoretical methods for the selection of antioxidant drugs and the rapid methods of evaluation: the 1,1‐diphenyl‐2‐picrylhydrazyl radical and the thiobarbituric acid reactive substances in the lipid peroxidation initiated by Fe2+ and ascorbic acid in human erythrocytes. The associate derivatives exhibited a more potent inhibition than the salicylic acid, while the benzoyl compound exhibited a more potent inhibition than paracetamol. The molecular parameters related to the electron distribution and structure (ionization potential and energy of the highest occupied molecular orbital) correlated very well with the antioxidant action of the compounds studied here in different tests. The drug design and evaluation of the free radical scavenging effect for the molecular association of 4‐aminophenol and salicylate derivatives using DFT methods and the rapid methods of evaluation DPPH and TBARS. The associate derivatives exhibited a more potent inhibition than the salicylic acid, while the benzoyl compound exhibited a more potent inhibition than paracetamol.
ISSN:1747-0277
1747-0285
DOI:10.1111/cbdd.12096