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Structure–Antioxidant Activity Relationships in a Series of NO‐Donor Phenols
Author(s) -
Tosco Paolo,
Marini Elisabetta,
Rolando Barbara,
Lazzarato Loretta,
Cena Clara,
Bertinaria Massimo,
Fruttero Roberta,
Reist Marianne,
Carrupt PierreAlain,
Gasco Alberto
Publication year - 2008
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.200800101
Subject(s) - phenols , antioxidant , series (stratigraphy) , chemistry , stereochemistry , organic chemistry , biology , paleontology
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 Δ H abs , which describes the enthalpy of homolytic OH 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.