Fluorine-substituted derivatives of the carcinogenic dihydrodiol and diol epoxide metabolites of 7-methyl-, 12-methyl- and 7,12-dimethylbenz[a]anthracene

Article abstract of DOI:10.1016/S0040-4020(97)00409-2

Stereospecific syntheses of the trans-3,4-dihydrodiol metabolites of 9- and 10-fluoro-7, 12-dimethylbenz[alanthracene, -7-methylbenz[a]anthracene, and -12-methylbenz[a]anthracene are described. These dihydrodiols are putative proximate carcinogenic metabolites that undergo activation by the P-450 microsomal enzymes to ultimate carcinogenic anti- and syn-diol epoxide metabolites that bind to nucleic acids in vivo. Syntheses of several of the anti- diol epoxide metabolites are also described.