title: Synthesis of enantiomers of exo-2-norbornyl-N-n-butylcarbamate and endo-2-norbornyl-N-n-butylcarbamate for stereoselective inhibition of acetylcholinesterase.
abstract: 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.
authors.affiliation: Department of Neurosurgery, Chung Shan Medical University Hospital, Taichung, Taiwan.
authors.forename: Shyh-Ying
authors.initials: SY
authors.lastname: Chiou
authors.forename: Chuan-Fu
authors.initials: CF
authors.lastname: Huang
authors.forename: Shyh-Jei
authors.initials: SJ
authors.lastname: Yeh
authors.forename: I-Ru
authors.initials: IR
authors.lastname: Chen
authors.forename: Gialih
authors.initials: G
authors.lastname: Lin
mesh_terms: 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
chemical_list: C549224:2-norbornyl-N-n-butylcarbamate; D002219:Carbamates; D002800:Cholinesterase Inhibitors; D017953:Isocyanates; D009636:Norbornanes; D000110:Acetylcholinesterase; C002509:butyl isocyanate