en
Scientific article
English

Structure-antioxidant activity relationships in a series of NO-donor phenols

Published inChemMedChem, vol. 3, no. 9, p. 1443-1448
Publication date2008
Abstract

Recently we reported a new class of NO-donor phenols that could be of interest in the treatment of many forms of cardiovascular disease (CD). Their potencies as inhibitors of ferrous salt/ascorbate-induced peroxidation of membrane lipids of rat hepatocytes were assessed as pIC(50) values through the TBARS assay. In this work we aimed to find quantitative relationships between the antioxidant activity of these compounds and appropriate molecular descriptors. In particular, we determined their log P(oct), their reactivity (log Z) in reaction with the 2,2-diphenyl-1-picrylhydrazyl radical (DPPH(.)), and the theoretical parameter DeltaH(abs), which describes the enthalpy of homolytic O--H bond cleavage. The QSAR equations found through the classical Hansch approach allowed us to draw interesting conclusions on the possible mechanisms of reaction with radicals in the various environments, while underlining the role of lipophilicity in antioxidant activity.

Keywords
  • Antioxidants/chemical synthesis/chemistry
  • Chemistry, Physical
  • Chromatography, High Pressure Liquid/methods
  • Free Radicals/chemistry
  • Molecular Structure
  • Nitric Oxide Donors/chemical synthesis/chemistry
  • Phenols/chemical synthesis/chemistry
  • Picrates/chemistry
  • Quantitative Structure-Activity Relationship
  • Stereoisomerism
  • Thermodynamics
  • Time Factors
Citation (ISO format)
TOSCO, Paolo et al. Structure-antioxidant activity relationships in a series of NO-donor phenols. In: ChemMedChem, 2008, vol. 3, n° 9, p. 1443–1448. doi: 10.1002/cmdc.200800101
Main files (1)
Article (Published version)
accessLevelRestricted
Identifiers
577views
0downloads

Technical informations

Creation11/06/2009 10:33:00 AM
First validation11/06/2009 10:33:00 AM
Update time03/14/2023 3:17:35 PM
Status update03/14/2023 3:17:34 PM
Last indexation01/15/2024 7:12:37 PM
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack