Monoamine oxidase-catalyzed oxidation of endo,endo-2-amino-6-[(Z)-2'-phenyl]ethenylbicyclo[2.2.1]heptane, a potential probe for a radical cation intermediate

Xueqing Wang; Richard B. Silverman

doi:10.1016/S0968-0896(00)00094-8

Monoamine oxidase-catalyzed oxidation of endo,endo-2-amino-6-[(Z)-2'-phenyl]ethenylbicyclo[2.2.1]heptane, a potential probe for a radical cation intermediate

Xueqing Wang, Richard B. Silverman^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

An 11-step synthesis of endo,endo-2-amino-6-[(E)-2'-phenyl]ethenylbicyclo[2.2.1]heptane (6) and the corresponding (Z)-isomer (7) was carried out in an attempt to make a compound that could trap the purported amine radical cation intermediate during monoamine oxidase (MAO)-catalyzed oxidation of amines. The E-isomer was not a substrate for MAO, and the Z-isomer was a very poor substrate. No trapping product was observed. Possible explanations for the inability of these compounds to trap a potential radical cation intermediate are discussed. Copyright (C) 2000 Elsevier Science Ltd.

Original language	English (US)
Pages (from-to)	1645-1651
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	8
Issue number	7
DOIs	https://doi.org/10.1016/S0968-0896(00)00094-8
State	Published - Jul 2000

Funding

We are grateful to the National Institutes of Health (Grant GM32634) for financial support of this research. We thank Charlotte Stern for the crystal structures.

ASJC Scopus subject areas

Drug Discovery
Molecular Medicine
Molecular Biology
Biochemistry
Clinical Biochemistry
Pharmaceutical Science
Organic Chemistry

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10.1016/S0968-0896(00)00094-8

Cite this

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title = "Monoamine oxidase-catalyzed oxidation of endo,endo-2-amino-6-[(Z)-2'-phenyl]ethenylbicyclo[2.2.1]heptane, a potential probe for a radical cation intermediate",

abstract = "An 11-step synthesis of endo,endo-2-amino-6-[(E)-2'-phenyl]ethenylbicyclo[2.2.1]heptane (6) and the corresponding (Z)-isomer (7) was carried out in an attempt to make a compound that could trap the purported amine radical cation intermediate during monoamine oxidase (MAO)-catalyzed oxidation of amines. The E-isomer was not a substrate for MAO, and the Z-isomer was a very poor substrate. No trapping product was observed. Possible explanations for the inability of these compounds to trap a potential radical cation intermediate are discussed. Copyright (C) 2000 Elsevier Science Ltd.",

author = "Xueqing Wang and Silverman, \{Richard B.\}",

note = "Funding Information: We are grateful to the National Institutes of Health (Grant GM32634) for financial support of this research. We thank Charlotte Stern for the crystal structures.",

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AU - Wang, Xueqing

AU - Silverman, Richard B.

N1 - Funding Information: We are grateful to the National Institutes of Health (Grant GM32634) for financial support of this research. We thank Charlotte Stern for the crystal structures.

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Monoamine oxidase-catalyzed oxidation of endo,endo-2-amino-6-[(Z)-2'-phenyl]ethenylbicyclo[2.2.1]heptane, a potential probe for a radical cation intermediate

Abstract

Funding

ASJC Scopus subject areas

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CCDC 150183: Experimental Crystal Structure Determination

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Monoamine oxidase-catalyzed oxidation of endo,endo-2-amino-6-[(Z)-2'-phenyl]ethenylbicyclo[2.2.1]heptane, a potential probe for a radical cation intermediate

Abstract

Funding

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 150183: Experimental Crystal Structure Determination

Cite this