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SYNTHESIS OF MERCAPTURIC ACID-DERIVATIVES OF PUTATIVE TOXIC METABOLITES OF BROMOBENZENE

被引：43
作者：
HANZLIK, RP
WELLER, PE
DESAI, J
ZHENG, J
HALL, LR
SLAUGHTER, DE
机构：
[1] Department of Medicinal Chemistry, University of Kansas, Lawrence
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 09期
关键词：
D O I：
10.1021/jo00296a034
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis and characterization of nine isomerically defined S-arylmercapturic acids of interest in connection withthe metabolism of the model hepatotoxin bromobenzene is described. Included are three S-(bromophenyl)-, two S-(bromohydroxyphenyl)-, and three S-(bromodihydroxyphenyl)mercapturic acids of defined substitution pattern. In addition, several related compounds with two or no bromine atoms are described. These syntheses depend on two basic methods, 1,4-addition of various arene thiols to acetamidoacrylic acid or the 1,4-addition of N-acetyl-L-cysteine to various benzoquinone derivatives. In addition, we describe a method for efficient conversion of the mercapturic acids to thioanisole derivatives, regioisomers of which can be separated and detected at low levels by capillary gas-liquid chromatography. © 1990, American Chemical Society. All rights reserved.
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收藏
页码：2736 / 2742
页数：7
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