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標題: Benzene-1,2-, 1,3-, and 1,4-di-N-substituted carbamates as conformationally constrained inhibitors of acetylcholinesterase
作者: Lin, M.C.
Hwang, M.T.
Chang, H.G.
Lin, C.S.
Lin, G.
關鍵字: acetylcholinesterase;carbamate;conformation;inhibitor;structure-reactivity relationships;pancreatic cholesterol esterase;butyrylcholinesterase;cholinesterases;recognition;mechanism;site
Project: Journal of Biochemical and Molecular Toxicology
期刊/報告no:: Journal of Biochemical and Molecular Toxicology, Volume 21, Issue 6, Page(s) 348-353.
Benzene-1,2-, 1,3-, and 1,4-di-N-substituted carbamates (1-15) are synthesized as the conformationally constrained inhibitors of acetylcholinesterase and mimic gauche, eclipsed, and anti-conforinations of acetylcholine, respectively. All carbamates 1-15 are characterized as the pseudo substrate inhibitors of acetylcholinesterase. For a series of geometric isomers, the inhibitory potencies are as follows: benzene-1,4-di-N-substituted carbamate (para compound)> benzene-1,3-di-N-substituted carbamate (meta compound) > benzene-1,2-di-N-substituted carbarnate (ortho compound). Therefore, benzene1,4-di-N-substituted carbamates (para compounds), with the angle of 180 degrees between two C(benzene)-O bonds, mimic the preferable anti C-O/C-N conformers of acetylcholine for the choline ethylene backbone in the acetylcholinesterase catalysis. (c) 2007 Wiley Periodicals, Inc.
ISSN: 1095-6670
DOI: 10.1002/jbt.20202
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