Comparative QSAR and radical toxicology: the aromatic CH2OH moiety

Abstract

Evidence is summarized to show via quantitative structure–activity relationships (QSAR) that the aromatic CH₂OH group when conjugated with electron-releasing substituents displays toxic effects that suggest a radical reaction mechanism. The evidence can be used to explain the inhibitory action of lucanthone toward schistosomiasis. That is, lucanthone per se is not active, but its metabolite in which a methyl group has been converted to CH₂OH is. This calls to mind the activity of chloramphenicol, which was a very effective anti-bacterial agent, but also caused serious blood dyscrasias in some patients. Presumably this could have been due to the toxic action of radicals.