39484-08-7Relevant academic research and scientific papers
Synthesis of Mercapturic Acid Derivatives of Putative Toxic Metabolites of Bromobenzene
Hanzlik, Robert P.,Weller, Paul E.,Desai, Jayant,Zheng, Jiang,Hall, Larry R.,Slaughter, Donald E.
, p. 2736 - 2742 (2007/10/02)
The synthesis and characterization of nine isomerically defined S-arylmercapturic acids of interest in connection with the 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 separed and detected at low levels by capillary gas-liquid chromatography.
