trans,trans-1-(Aminomethyl)-2-methoxy-3-phenylcyclopropane (3) was synthesized in three steps from (Z)-β-methoxystyrene and ethyl diazoacetate. Compound 3 was shown to be a substrate and inactivator of mitochondrial beef liver monoamine oxidase (MAO) with a partition ratio of 1428. MAO-catalyzed oxidation of 3 produces one major metabolite, isolated and identified by GCOSY, GHMQC, and GHMBC NMR techniques to be frans,frarcs-2-methoxy-3-phenyl-l-Ar-[(3-phenyl-JV-pyrrolyl)methyl]cyclopropane (7). A mechanism, supported by a model reaction, is proposed for the formation of this metabolite.
ASJC Scopus subject areas
- Organic Chemistry