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Paper | Special issue | Vol 50, No. 1, 1999, pp.95-102
Published online, 1st January, 1970
DOI: 10.3987/COM-98-S(H)3
4'-Hydroxyphenylcarbamates of (3aS)-Eseroline and (3aS)-N(1)-Noreseroline: Potential Metabolites of the Alzheimer's Anticholinesterase Drug Phenserine

Qian-sheng Yu, Nigel H. Greig,* Harold W. Holloway, and Arnold Brossi

*Drug Design & Development, Laboratory of Cellular & Molecular Biology, Gerontology Research Center, LCMB/DDD/Room 4-B-02, National Institute on Aging, Intramural Program, 5600 Nathan Shock Drive, Baltimore, Maryland 21224-6825, U.S.A.


4’-Hydroxyphenylcarbamates of (3aS)-eseroline (3) and (3aS)-N(1)-noreseroline (4), as predicted metabolites of phenserine (1), were synthesized. Biological evaluation showed that 3 and 4 possessed potent activities for inhibition of acetylcholinesterase and butyrylcholinesterase in vitro. In contrast the ontermediates, 4’-benzyloxyphenserine (8) and 4’-benzyloxy N(1)-benzylphenserine (12), demonstrated unusually potent and selective activities against butyrylcholinesterase.