Sims P
Biochem J. 1972 Nov;130(1):27-35. doi: 10.1042/bj1300027.
The synthesis of dibenz[a,c]anthracene 10,11-oxide is described. The oxide was unstable and was rapidly decomposed with cold mineral acid into a mixture of 10- and 11- hydroxydibenz[a,c]anthracene. The oxide was converted by rat liver microsomal preparations and homogenates into a product that is probably 10,11-dihydro-10,11-dihydroxydibenz[a,c]anthracene and which was identical with the metabolite formed when dibenz[a,c]anthracene was metabolized by rat liver homogenates. The oxide did not react either chemically or enzymically with GSH. 10,11-Dihydrodibenz[a,c]anthracene and 10,11-dihydrodibenz[a,c]anthracene 12,13-oxide were both metabolized by rat liver preparations into trans-10,11,12,13-tetrahydro-10,11-dihydroxydibenz[a,c] anthracene and the oxide was converted chemically into this dihydroxy compound, and it reacted chemically but not enzymically with GSH. In the alkylation of 4-(p-nitrobenzyl)pyridine, the ;K-region' epoxide, dibenz[a,h]anthracene 5,6-oxide, was more active than either dibenz[a,c]anthracene 10,11-oxide or 10,11-dihydrobenz[a,c]anthracene 12,13-oxide.
描述了二苯并[a,c]蒽10,11 - 氧化物的合成。该氧化物不稳定，在冷的无机酸作用下迅速分解为10 - 和11 - 羟基二苯并[a,c]蒽的混合物。该氧化物经大鼠肝脏微粒体制剂和匀浆转化为一种产物，可能是10,11 - 二氢 - 10,11 - 二羟基二苯并[a,c]蒽，且与二苯并[a,c]蒽经大鼠肝脏匀浆代谢形成的代谢产物相同。该氧化物在化学或酶促反应中均不与谷胱甘肽（GSH）反应。10,11 - 二氢二苯并[a,c]蒽和10,11 - 二氢二苯并[a,c]蒽12,13 - 氧化物均经大鼠肝脏制剂代谢为反式 - 10,11,12,13 - 四氢 - 10,11 - 二羟基二苯并[a,c]蒽，且该氧化物可化学转化为这种二羟基化合物，它在化学上能与GSH反应，但酶促反应中不反应。在4 - （对硝基苄基）吡啶的烷基化反应中，“K - 区域”环氧化物二苯并[a,h]蒽5,6 - 氧化物比二苯并[a,c]蒽10,11 - 氧化物或10,11 - 二氢苯并[a,c]蒽12,13 - 氧化物更具活性。
