Synthesis of 6-methylchrysene-l,2-diol-3,4-epoxides and comparison of their mutagenicity to 5-methylchrysene-l,2-diol-3,4-epoxides

The syn- and anti-isomers of l,2-dihydroxy-3,4-epoxy-l,2,3,4-tetrahydro-6-methykhrysene (6-MeC-l,2-diol-3,4-epoxide) were synthesized and their mutagenk activities in Salmonella typhimurium were compared with those of the syn- and anti-isomers of l,2-dihydroxy-3,4-epoxy-l,2,3,4-tetrahydro-5-methykhrysene (5-MeC-l,2-diol-3,4-epoxide). The most mu-tagenic compound was anti-5-MeC-l,2-diol-3,4-epoxide, followed by syn-5-MeC-l,2-diol-3,4-epoxide. At the same doses, neither of the 6-MeC-l, 2-dioI-3, 4-poxides was mutagenic. These results demonstrate the enhancing effect on mutagenicity of a methyl group in the same bay region as the epoxide ring of a diol epoxide.