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Synthesis of doubly 15‐nitrogen labelled N‐[4‐hydroxybutyl]‐N‐nitrosobutylamine, a potent urinary bladder carcinogen in animals
Author(s) -
Boigegrain Rose Anne,
Fanelli Roberto,
Gariboldi Pierluigi,
Airoldi Luisa
Publication year - 1988
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580251015
Subject(s) - chemistry , amine gas treating , medicinal chemistry , nitroso , hydrazine (antidepressant) , chloramine , phthalimide , moiety , hydroxylation , formic acid , organic chemistry , chlorine , chromatography , enzyme
The labelled precursors for the amino nitrogen atom was 15 N‐potassium phthalimide which was condensed with triphenylmethyloxychlorobutane. The phthalimide group was then cleaved with hydrazine and the primary amine obtained was condensed with butyraldehyde followed by sodium borohydride reduction to give the secondary amine N‐[4‐triphenylmethyloxybutyl]butyl‐[ 15 N]amine. After deprotection of the triphenylmethyl group with trifluoroacetic acid, the amino alcohol obtained was nitrosated with 15 N‐sodium nitrite in hydrochloric acid medium to give N‐[4‐hydroxybutyl]‐N‐[ 15 N]nitrosobutyl[ 15 N]amine. The two 15‐nitrogen atoms were incorporated in order to obtain a tool useful for studying the metabolic activation of this compound. The evolution of labelled molecular nitrogen will be used to quantify the extent of nitrosamine hydroxylation at the carbon atom α to the nitroso moiety.