Stillwell W G, Bouwsma O J, Thenot J P, Horning M G, Griffin G W, Ishikawa K, Takaku M
Res Commun Chem Pathol Pharmacol. 1978 Jun;20(3):509-30.
Eight methylthio metabolites have been found as urinary products of the metabolism of naphthalene in the rat. One was 1-methylthionaphthalene. A second was a methylthio analog and the dihydrodiol, and a third was naphthalene substituted with one hydroxyl and one methylthio group. Two compounds with common structural elements were found; one of these was prepared by synthesis from anti-1,2:3,4-naphthalene dioxide and one from 1 beta, 2 alpha-dithyroxy-3 alpha, 4 alpha-epoxy-1,2,3,4-tetrahydronaphthalene by reaction with 2-keto-4-methylthiobutyric acid or with methionine. Each of these compounds contained one methythio group and three hydroxyl groups substituted on a tetrahydronaphthalene structure. Two metabolites with two methylthio groups and two hydroxyl substituents on a tetrahydronaphthalene ring were also detected; one of these was prepared by synthesis from the dioxide. The most likely metabolic origin of these methylthio metabolites is through the reaction of epoxides (including the diepoxide) with a nucleophile which may be methyl mercaptan, 2-keto-4-methylthiobutyric acid, or methionine.
已发现八种甲硫基代谢物是大鼠体内萘代谢的尿液产物。一种是1-甲硫基萘。第二种是甲硫基类似物和二氢二醇，第三种是被一个羟基和一个甲硫基取代的萘。发现了两种具有共同结构元素的化合物；其中一种是由反式-1,2:3,4-萘二氧化物合成制备的，另一种是由1β,2α-二羟基-3α,4α-环氧-1,2,3,4-四氢萘与2-酮-4-甲硫基丁酸或蛋氨酸反应制备的。这些化合物中的每一种都含有一个甲硫基和三个取代在四氢萘结构上的羟基。还检测到两种在四氢萘环上带有两个甲硫基和两个羟基取代基的代谢物；其中一种是由二氧化物合成制备的。这些甲硫基代谢物最可能的代谢来源是环氧化物（包括二环氧物）与亲核试剂的反应，亲核试剂可能是甲硫醇、2-酮-4-甲硫基丁酸或蛋氨酸。
