Chemical rearrangement of phenol-epoxide metabolites of polycyclic aromatic hydrocarbons to quinone-methides.
Chemical rearrangement of phenol-epoxide metabolites of polycyclic aromatic hydrocarbons to quinone-methides.
复制标题
多环芳烃的苯酚环氧化物代谢物化学重排为醌甲基化物。
DOI：
10.1016/0006-291x(83)91550-4
复制
发表时间：
1983
影响因子：
3.1
通讯作者：
P. Grover
中科院分区：
文献类型：
--
作者：
P. B. Hulbert;P. Grover
关于三醇环氧化物和酚环氧化物代谢物参与多环烃代谢活化的证据正在积累。有人提出，在这些环氧化物中存在的酚羟基会激活环氧化物，并允许它们重排为醌类化合物。这些醌类化合物具有高度活性，具有很强的烷基化活性，是潜在可分离的化学实体。在一种共振形式中，它们是共振稳定的碳离子。只有在某些位置上也含有酚羟基的环氧化合物才能形成醌类化合物：这些化合物包括9-羟基苯基[a]芘4,5 -氧化物和9-羟基反式- 1,2 -二氢- 1,2 -二羟基芘3,4 -氧化物和2-羟基反式- 9,10 -二氢- 9,10 -二羟基苯基[a]芘7,8 -氧化物。
Evidence for the involvement of triol-epoxide and phenol-epoxide metabolites in the metabolic activation of polycyclic hydrocarbons is accumulating. It is proposed that the phenolic OH-groups present in such epoxides will activate the epoxide moieties and permit their rearrangement to quinone-methides. These quinone-methides are highly reactive, potentially-isolable chemical entities with strong alkylating activity. In one resonance form they are resonance-stabilized carbonium ions. Only epoxides that also possess phenolic OH-groups in certain positions will form quinone-methides: these appear to include 9-hydroxybenzo [a] pyrene 4, 5-oxide and the triol-epoxides 9-hydroxy-trans-1, 2-dihydro-1, 2-dihydroxychrysene 3, 4-oxide and 2-hydroxy-trans-9, 10-dihydro-9, 10-dihydroxybenzo [a] pyrene 7, 8-oxide.
影响因子：
7.3
作者：
I. Antonini;T. Lin;L. A. Cosby;Y. Dai;A. Sartorelli
通讯作者：
I. Antonini;T. Lin;L. A. Cosby;Y. Dai;A. Sartorelli