| Abstract: | A series of oxidized derivatives of 10-deuterobenzol[a]pyrene (10-D-BaP) were synthesized. Oxidation of 10-D-BaP with sodium dichromate dihydrate yielded the 1,6-, 3,6-, and 6,12-quinones of 10-D-Bap. Upon electrophilic aromatic substitution of 10-D-BaP with sodium nitrate, N-bromosuccinimide, and N-chlorosuccinimide we were afforded 6-nitro-10-D-BaP, 6-bromo-10-D-BaP, and 6-chloro-10-D-BaP, respectively, in high yields. The Vilsmier-Haack reaction of 10-D-BaP provided 6-formyl-10-D-BaP which upon reduction with sodium borohydride, yielded 6-hydroxymethyl-10-D-BaP. Reduction with hydrazine in n-amyl alcohol gave 6-methyl-10-D-BaP. Reduction of 6-nitro-10-D-BaP with hydrazine and Pd/C yielded 6-amino-10-D-BaP. The synthesized compounds, which are known metabolites of benzo[a]pyrene and are useful substrates for metabolism, are important compounds for mechanistic study of the chemical carcinogenesis by benzo[a]pyrene. |
