Functionalization of the alicyclic skeleton of epibatidine: synthesis and nicotinic acetylcholine receptor binding affinities of epibatidine analogues.
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.
Wei
Zhi-Liang
ZL
Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood Street, Chicago, Illinois 60612-7231, USA.
Xiao
Yingxian
Y
George
Clifford
C
Kellar
Kenneth J
KJ
Kozikowski
Alan P
AP
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
D018712:Analgesics, Non-Narcotic; D019086:Bridged Bicyclo Compounds, Heterocyclic; D011725:Pyridines; D011978:Receptors, Nicotinic; C082748:epibatidine; D012825:Silicon