Xl. Lu et al., MONOAMINE OXIDASE-CATALYZED OXIDATIVE REARRANGEMENT OF ANS-1-(AMINOMETHYL)-2-METHOXY-3-PHENYLCYCLOPROPANE, Journal of organic chemistry, 61(25), 1996, pp. 8961-8966
ans-1-(Aminomethyl)-2-methoxy-3-phenylcyclopropane (3) was synthesized
in three steps from (Z)-beta-methoxystyrene and ethyl diazoacetate. C
ompound 3 was shown to be a substrate and inactivator of mitochondrial
beef liver monoamine oxidase (MAO) with a partition ratio of 1428. MA
O-catalyzed oxidation of 3 produces one major metabolite, isolated and
identified by GCOSY, GHMQC, and GHMBC NMR techniques to be methoxy-3-
phenyl-1-N-[(3-phenyl-N-pyrrolyl)methyl] cyclopropane (7). A mechanism
, supported by a model reaction, is proposed for the formation of this
metabolite.