Synthesis of isothiocyanate-derived mercapturic acids

M Vermeulen, B Zwanenburg, GJF Chittenden…

Index: Vermeulen, Martijn; Zwanenburg, Binne; Chittenden, Gordon J.F.; Verhagen, Hans European Journal of Medicinal Chemistry, 2003 , vol. 38, # 7-8 p. 729 - 737

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Citation Number: 44

Abstract

Twelve mercapturic acids derived from saturated and unsaturated aliphatic and aromatic isothiocyanates were synthesised, by adding isothiocyanate to a solution of N-acetyl-l- cysteine and sodium bicarbonate, in a typical yield of 77%. Isothiocyanates were synthesised first by adding the corresponding alkyl bromide to phthalimide potassium salt. The obtained N-alkyl-phthalimide was hydrazinolysed yielding the alkyl amine, which ...