F. Compernolle, N. Castagnoli
1982
Citations
0
Influential Citations
3
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
This paper describes the synthesis and preliminary metabolic studies on N,N-dimethyl-N′-2-imidazolyl-N′-benzyl-1,2-ethanediamine (compound 12), an imidazole analog of the carcinogenic antihistamine methapyrilene. The 2-aminoimidazole starting material is carried through a five-step reaction sequence which involves introduction of the benzyl and dimethylaminoethyl side chains via sequential acylation of the 2-amino group and reduction of each intermediate amide. Metabolic studies on compound 12 and a d2-analog were performed with rabbit liver microsomes. Chemical ionization mass spectral analysis indicates the presence of metabolites formed by N-demethylation and imidazole C-oxidation. In addition, a seven membered ring metabolite has been identified which apparently is formed by intramolecular cyclization of an intermediate methylene iminium ion.