Synthesis of enantiomers of exo-2-norbornyl-N-n-butylcarbamate and endo-2-norbornyl-N-n-butylcarbamate for stereoselective inhibition of acetylcholinesterase.
The acetylcholinesterase inhibition by enantiomers of exo- and endo-2-norbornyl-N-n-butylcarbamates shows high stereoselelectivity. For the acetylcholinesterase inhibitions by (R)-(+)- and (S)-(-)-exo-2-norbornyl-N-n-butylcarbamates, the R-enantiomer is more potent than the S-enantiomer. But, for the acetylcholinesterase inhibitions by (R)-(+)- and (S)-(-)-endo-2-norbornyl-N-n-butylcarbamates, the S-enantiomer is more potent than the R-enantiomer. Optically pure (R)-(+)-exo-, (S)-(-)-exo-, (R)-(+)-endo-, and (S)-(-)-endo-2-norbornyl-N-n-butylcarbamates are synthesized from condensations of optically pure (R)-(+)-exo-, (S)-(-)-exo-, (R)-(+)-endo-, and (S)-(-)-endo-2-norborneols with n-butyl isocyanate, respectively. Optically pure norborneols are obtained from kinetic resolutions of their racemic esters by lipase catalysis in organic solvent.
Chiou
Shyh-Ying
SY
Department of Neurosurgery, Chung Shan Medical University Hospital, Taichung, Taiwan.
Huang
Chuan-Fu
CF
Yeh
Shyh-Jei
SJ
Chen
I-Ru
IR
Lin
Gialih
G
D000110:Acetylcholinesterase / Q000187:drug effects* / Q000378:metabolism; D002219:Carbamates / Q000138:chemical synthesis* / Q000737:chemistry; D002800:Cholinesterase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D017953:Isocyanates / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D009636:Norbornanes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
C549224:2-norbornyl-N-n-butylcarbamate; D002219:Carbamates; D002800:Cholinesterase Inhibitors; D017953:Isocyanates; D009636:Norbornanes; D000110:Acetylcholinesterase; C002509:butyl isocyanate