4 '-hydroxyphenylcarbamates of (3aS)-eseroline and (3aS)-N(1)-noreseroline: Potential metabolites of the Alzheimer's anticholinesterase drug phenserine
Qs. Yu et al., 4 '-hydroxyphenylcarbamates of (3aS)-eseroline and (3aS)-N(1)-noreseroline: Potential metabolites of the Alzheimer's anticholinesterase drug phenserine, HETEROCYCLE, 50(1), 1999, pp. 95-102
4'-Hydroxyphenylcarbamates of (3aS)-eseroline (3) and (3aS)-N(1)-noreseroli
ne (4), as predicted metabolites of phenserine (1), were synthesized. Biolo
gical evaluation showed that 3 and 4 possessed potent activities for inhibi
tion of acetylcholinesterase and butyrylcholinesterase in vitro. In contras
t the intermediates, 4'-benzyloxyphenserine (8) and 4'-benzyloxy N(1)-benzy
lphenserine (12), demonstrated unusually potent and selective activities ag
ainst butyrylcholinesterase.