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.

引用

页码：2736 / 2742

页数：7

共 34 条

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