title: Functionalization of the alicyclic skeleton of epibatidine: synthesis and nicotinic acetylcholine receptor binding affinities of epibatidine analogues.
abstract: A novel method for the epimerization of endo-2-(6-chloro-3-pyridyl)-7-azabicyclo[2.2.1]heptan-3-one (12) on silica gel was developed and used as the key step to synthesize functionalized analogues of epibatidine which were evaluated for their nicotine receptor subtype selectivity in binding studies.
authors.affiliation: Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood Street, Chicago, Illinois 60612-7231, USA.
authors.forename: Zhi-Liang
authors.initials: ZL
authors.lastname: Wei
authors.forename: Yingxian
authors.initials: Y
authors.lastname: Xiao
authors.forename: Clifford
authors.initials: C
authors.lastname: George
authors.forename: Kenneth J
authors.initials: KJ
authors.lastname: Kellar
authors.forename: Alan P
authors.initials: AP
authors.lastname: Kozikowski
mesh_terms: D018712:Analgesics, Non-Narcotic / Q000138:chemical synthesis / Q000737:chemistry; D000818:Animals; D001001:Anura; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D007700:Kinetics; D008956:Models, Chemical; D008958:Models, Molecular; D011485:Protein Binding; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D011978:Receptors, Nicotinic / Q000737:chemistry* / Q000378:metabolism; D012825:Silicon; D014055:Tomography, Emission-Computed; D014965:X-Rays
chemical_list: D018712:Analgesics, Non-Narcotic; D019086:Bridged Bicyclo Compounds, Heterocyclic; D011725:Pyridines; D011978:Receptors, Nicotinic; C082748:epibatidine; D012825:Silicon