Methylbenz[a]anthracenes: Correlations between theoretical reactivity indices and carcinogenicity

Abstract

Methyl substitution in benz[a]anthracene leads to isomeric derivatives with distinctly different carcinogenic potencies. These differences in carcinogenic activity can be explained by examining the presumed in vivo metabolic transformations of these compounds using molecular orbital reactivity indices. Good correlations are found between carcinogenic activity and properties of later metabolites. Epoxidation of a dihydrodiol intermediate and the ability to form a stable “bay region” carbonium ion appear to be important factors in carcinogenic potency.