1,6-和3,6-二硝基苯并[a]芘的合成、化学性质及致突变性

Synthesis, chemical properties and mutagenicity of 1,6- and 3,6-dinitrobenzo[a]pyrenes.

作者信息

Fukuhara K, Miyata N, Matsui M, Matsui K, Ishidate M, Kamiya S

机构信息

National Institute of Hygienic Sciences, Tokyo, Japan.

出版信息

Chem Pharm Bull (Tokyo). 1990 Nov;38(11):3158-61. doi: 10.1248/cpb.38.3158.

DOI:10.1248/cpb.38.3158

PMID:2085901

Abstract

Nitration of benzo[a]pyrene (BaP) with HNO3 (d = 1.38) produced a mixture of dinitroBaPs (1,6- and 3,6-isomers) and mononitroBaPs (1-, 3- and 6-isomers). Pure 1,6-dinitroBaP and 3,6-dinitroBaP were obtained by the reduction of the dinitroBaPs mixture with NaSH to yield the separable products 1-amino-6-nitroBaP and 3-amino-6-nitroBaP, followed by conversion to dinitroBaPs via the the diazonium salts. The half-wave potentials (E1/2) corresponding to the one-electron reduction of dinitroBaPs were measured and the relationship of these values to the mutagenicity is discussed.

摘要

用硝酸（密度 = 1.38）对苯并[a]芘（BaP）进行硝化反应，生成了二硝基苯并[a]芘（1,6 - 和3,6 - 异构体）和单硝基苯并[a]芘（1 - 、3 - 和6 - 异构体）的混合物。通过用硫氢化钠还原二硝基苯并[a]芘混合物，得到可分离的产物1 - 氨基 - 6 - 硝基苯并[a]芘和3 - 氨基 - 6 - 硝基苯并[a]芘，随后通过重氮盐将其转化为二硝基苯并[a]芘，从而获得了纯的1,6 - 二硝基苯并[a]芘和3,6 - 二硝基苯并[a]芘。测量了与二硝基苯并[a]芘单电子还原相对应的半波电位（E1/2），并讨论了这些值与致突变性的关系。