Comparative QSAR: radical toxicity and scavenging. Two different sides of the same coin.
From an analysis of the toxicity of phenols to rat embryos and anilines to embryo fibroblast cells a new type of toxicity is postulated for these classes of compounds. Substituents which increase the electron density on the aromatic ring as estimated by sigma + or epsilon HOMO increase potency. It is postulated that it is the radical form of the phenols and the anilines that accounts for their toxicity. The results are compared with QSAR for radical scavengers and oxidoreductases acting on phenols, anilines and carbazoles.
Hansch
C
C
Chemistry Department, Pomona College, Claremont, California 91711-6338, USA.
Zhang
L
L
D000814:Aniline Compounds / Q000737:chemistry / Q000633:toxicity*; D000818:Animals; D002227:Carbazoles / Q000633:toxicity; D004622:Embryo, Mammalian / Q000166:cytology / Q000187:drug effects*; D005347:Fibroblasts / Q000187:drug effects; D016166:Free Radical Scavengers / Q000737:chemistry / Q000633:toxicity*; D015227:Lipid Peroxidation / Q000187:drug effects; D051379:Mice; D008956:Models, Chemical; D015394:Molecular Structure; D010088:Oxidoreductases / Q000737:chemistry; D010636:Phenols / Q000737:chemistry / Q000633:toxicity*; D051381:Rats; D013329:Structure-Activity Relationship
D000814:Aniline Compounds; D002227:Carbazoles; D016166:Free Radical Scavengers; D010636:Phenols; D010088:Oxidoreductases