Study of the intramolecular cyclization of N-methyl-3-phenyl-N-(2-(E)-phenylethenyl)-trans(cis)-oxiranecarboxamide--syntheses of Homoclausenamide and Dehydroclausenamide

Nianchun Ma; Kemei Wu; Liang Huang

doi:10.1016/j.ejmech.2007.11.022

Study of the intramolecular cyclization of N-methyl-3-phenyl-N-(2-(E)-phenylethenyl)-trans(cis)-oxiranecarboxamide--syntheses of Homoclausenamide and Dehydroclausenamide

Eur J Med Chem. 2008 Aug;43(8):1781-4. doi: 10.1016/j.ejmech.2007.11.022. Epub 2007 Dec 7.

Authors

Nianchun Ma¹, Kemei Wu, Liang Huang

Affiliation

¹ Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050, China. [email protected]

PMID: 18191305
DOI: 10.1016/j.ejmech.2007.11.022

Abstract

Homoclausenamide was synthesized for the first time, and the intramolecular cyclization study of N-methyl-3-phenyl-N-(2-(E)-phenylethenyl)-trans(cis)-oxiranecarboxamide well demonstrated how the stereochemistry affects the cyclization paths.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemistry*
Cyclization
Ethylene Oxide / chemistry*
Hydrogen / chemistry*
Lactams / chemical synthesis*
Lactams / chemistry
Lignans / chemical synthesis*
Lignans / chemistry
Methylation
Molecular Structure
Structure-Activity Relationship

Substances

Amides
Lactams
Lignans
clausenamide
Hydrogen
Ethylene Oxide