- 作者: Kim,Youngmee ; Jun,Moo-Jin ; 符必成 等
- 作者服務機構: National Center for Toxicological Research, U.S.A.
- 中文摘要: A series of oxidized derivatives of 10-deuterobenzo(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 importamt compounds for mechanistic study of the chemical carcinogenesis by benzo(a) pyrene.
- 英文摘要: --
- 中文關鍵字: 10-Deuterobenzo[A]Pyrene; Nitration; Bromination; Chlorination; Formylation
- 英文關鍵字: 硝化作用;溴化作用;氯化作用;甲烯化