Racemic N1-norphenserine and its enantiomers: Unpredicted inhibition of human acetyl- and butyrylcholinesterase and β-amyloid precursor protein in vitro
The optically pure enantiomers of N1-norphenserine (15, 16) were synthesized and its racemate 17 was prepared by mixing equal parts of each enantiomer. (-)-N1-Norphenserine (15) was prepared by partial synthesis initiated from the natural product, (-)-physostigmine (1). (+)-N 1-Norphenserine (16) was prepared by total synthesis using the Julian oxindole route, with modifications. The in vitro inhibitory activities of 15-17 were quantified against human erythrocyte AChE and plasma BChE as well as against human neuroblastoma cell β-amyloid precursor protein secretion in cell culture. All were active. Racemic compound (17) with a high AChE and β-amyloid precursor protein inhibitory action may warrant further assessment in Alzheimer's disease models.
Yu, Qian-Sheng,Luo, Weiming,Holloway, Harold W.,Utsuki, Tada,Perry, Tracy Ann,Lahiri, Debomoy K.,Greig, Nigel H.,Brossi, Arnold
p. 529 - 539
(2007/10/03)
Inhibition of Human Acetylcholinesterase by Unnatural (+)-(3aR)-N1-Norphysostigmine and Arylcarbamate Analogues
(+)-(3aR)-N1-Norphysostigmine (3b) and 3 arylcarbamate analogues (4b-6b) were prepared. They are less active inhibitors of human acetyl- and butyrylcholinesterase than their (-)-(3aS)-enantiomers but retained considerable activity.
Pei, Xue-Feng,Greig, Nigel H.,Bi, Sheng,Brossi, Arnold,Toome, V.
p. 265 - 270
(2007/10/03)
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