Synthesis of metabolites of 7,12-dimethylbenz[a]anthracene. 4-Hydroxy-7,12-dimethylbenz[a]anthracene, 7-hydroxymethyl-12-methylbenz[a]anthracene, their methyl ethers, and acetoxy derivatives.
Synthesis of metabolites of 7,12-dimethylbenz[a]anthracene. 4-Hydroxy-7,12-dimethylbenz[a]anthracene, 7-hydroxymethyl-12-methylbenz[a]anthracene, their methyl ethers, and acetoxy derivatives.
复制标题
7,12-二甲基苯并[a]蒽代谢物的合成。
DOI：
10.1021/jm00317a040
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发表时间：
1967
影响因子：
7.3
通讯作者：
D. R. Kelley
中科院分区：
文献类型：
--
作者：
J. W. Flesher;S. Soedigdo;D. R. Kelley
4-羟基-7，12-二甲基苯并[a]蒽（V）的合成是由已知的4-甲氧基苯并[o]蒽（I）的制备开始的方案完成的。将其氧化成4-甲氧基苯并[a]蒽醌（II），将其用甲基碘化镁处理，并将格氏络合物缓慢加入到甲醇中的HI中，得到4-甲氧基-7-碘甲基-12-甲基苯并[a]蒽（III）。将其还原为4-甲氧基-7，12-二甲基苯并[a]蒽（IV），用HBr-AcOH裂解得到4-羟基-7，12-二甲基苯并[a]蒽（V）。以7-碘甲基-L ~ 2-甲基苯并[a]蒽（IX）为原料，合成了7-羟乙基-12-甲基苯并[a]蒽（X）。这是方便地从苯并[a]蒽醌（VII）通过格氏法制备的。将IX的二氧六环溶液转化为相应的羟基化合物。4- 1-羟基-7，12-二甲基苯并[o]蒽，7-羟甲基-12-甲基。在大鼠肝蒽中检出了苯并[a]蒽和7，12-二羟甲基苯并[a]蒽。致癌活性的初步数据
The synthesisof 4-hydroxy-7, 12-dimethylbenz [aJanthracene (V) was accomplished by a scheme starting with the preparation of known 4-methoxybenz [o] anthracene (I). This was oxidized to 4-methoxybenz [ojanthraquinone (II) which was treated with methylmagnesium iodide and the Grignard complex slowly added to HI in methanol affording 4-methoxy-7-iodomethyl-12-methylbenz [alanthracene (III). This was reduced to 4-me-thoxy-7, 12-dimethylbenz [a] anthracene (IV) which was cleaved with HBr-AcOH to give 4-hvdroxy-7, 12-dimethyl-benz [a] anthracene (V). 7-Hydroxyftiethyl-12-methylbenz [a] anthracene (X) was synthesized from 7-iodomethvl-L2-methylbenz [a] anthracene (IX). This was conveniently prepared from benz [a] anthraquinone (VII) by the Grignard method. A dioxane solution of IX was converted to the corresponding hydroxy compound. 4-1tydroxy-7, 12-dimethylbenz [o] anthracene, 7-hydroxymethyl-12-met. hylbenz [a] anthracene, and 7, 12-dihydroxyinethylbenz [a] anthracene were identified in rat liver anthracene. Preliminary data on carcinogenic activity