Sims P
Biochem J. 1973 Feb;131(2):405-13. doi: 10.1042/bj1310405.
The syntheses of 7,12-dimethylbenz[a]anthracene 5,6-oxide, 7-acetoxymethyl-12-methylbenz[a]anthracene 5,6-oxide and a product that appears to be mainly 7-hydroxymethyl-12-methylbenz[a]anthracene 5,6-oxide are described. The compounds readily rearranged to phenols in the presence of mineral acid, and 7,12-dimethylbenz[a]anthracene 5,6-oxide and its 7-hydroxymethyl derivative reacted slowly with water to yield trans-5,6-dihydro-5,6-dihydroxy-7,12-dimethylbenz[a] anthracene and trans-5,6-dihydro-5,6-dihydroxy-7-hydroxymethyl-12-methylbenz [a]anthracene respectively. Both epoxides were converted enzymically by rat liver microsomal fractions and homogenates into the related trans-dihydrodiols. The epoxides reacted chemically with GSH to form conjugates that were identical with the conjugates formed when the epoxides were incubated with rat liver homogenates. The GSH conjugates were more stable to acid than conjugates derived from other arene oxides. In the alkylation of 4-(p-nitrobenzyl)pyridine, 7,12-dimethyl-benz[a]anthracene 5,6-oxide was more active than the 5,6-oxides of 7-methylbenz[a]-anthracene and benz[a]anthracene.
本文描述了7,12 - 二甲基苯并[a]蒽5,6 - 氧化物、7 - 乙酰氧基甲基 - 12 - 甲基苯并[a]蒽5,6 - 氧化物以及一种似乎主要是7 - 羟甲基 - 12 - 甲基苯并[a]蒽5,6 - 氧化物的产物的合成方法。这些化合物在无机酸存在下容易重排为酚类，并且7,12 - 二甲基苯并[a]蒽5,6 - 氧化物及其7 - 羟甲基衍生物与水缓慢反应，分别生成反式 - 5,6 - 二氢 - 5,6 - 二羟基 - 7,12 - 二甲基苯并[a]蒽和反式 - 5,6 - 二氢 - 5,6 - 二羟基 - 7 - 羟甲基 - 12 - 甲基苯并[a]蒽。两种环氧化物都被大鼠肝脏微粒体部分和匀浆酶促转化为相关的反式二氢二醇。环氧化物与谷胱甘肽（GSH）发生化学反应形成缀合物，这些缀合物与环氧化物与大鼠肝脏匀浆孵育时形成的缀合物相同。GSH缀合物比源自其他芳烃氧化物的缀合物对酸更稳定。在4 - （对硝基苄基）吡啶的烷基化反应中，7,12 - 二甲基苯并[a]蒽5,6 - 氧化物比7 - 甲基苯并[a]蒽和苯并[a]蒽的5,6 - 氧化物更具活性。
