Heterocycles p. 529 - 539 (2003)
Update date:2022-09-26
Topics:
Yu, Qian-Sheng
Luo, Weiming
Holloway, Harold W.
Utsuki, Tada
Perry, Tracy Ann
Lahiri, Debomoy K.
Greig, Nigel H.
Brossi, Arnold
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.
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