TY - JOUR
T1 - Monoamine Oxidase-Catalyzed Oxidative Rearrangement of trans,trans-1-(Aminomethyl)-2-methoxy-3-phenylcyclopropane
AU - Lu, Xingliang
AU - Yang, Shengtian
AU - Silverman, Richard B.
PY - 1996
Y1 - 1996
N2 - 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.
AB - 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.
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U2 - 10.1021/jo961540a
DO - 10.1021/jo961540a
M3 - Article
C2 - 11667878
AN - SCOPUS:13044296834
SN - 0022-3263
VL - 61
SP - 8961
EP - 8966
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 25
ER -