Functionalization of the alicyclic skeleton of epibatidine: synthesis and nicotinic acetylcholine receptor binding affinities of epibatidine analogues

Zhi-Liang Wei; Yingxian Xiao; Clifford George; Kenneth J Kellar; Alan P Kozikowski

doi:10.1039/b308906a

Functionalization of the alicyclic skeleton of epibatidine: synthesis and nicotinic acetylcholine receptor binding affinities of epibatidine analogues

Org Biomol Chem. 2003 Nov 21;1(22):3878-81. doi: 10.1039/b308906a.

Authors

Zhi-Liang Wei¹, Yingxian Xiao, Clifford George, Kenneth J Kellar, Alan P Kozikowski

Affiliation

¹ Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood Street, Chicago, Illinois 60612-7231, USA.

PMID: 14664377
DOI: 10.1039/b308906a

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.

Publication types

Research Support, U.S. Gov't, P.H.S.

MeSH terms

Analgesics, Non-Narcotic / chemical synthesis
Analgesics, Non-Narcotic / chemistry
Animals
Anura
Bridged Bicyclo Compounds, Heterocyclic / chemical synthesis*
Bridged Bicyclo Compounds, Heterocyclic / chemistry*
Kinetics
Models, Chemical
Models, Molecular
Protein Binding
Pyridines / chemical synthesis*
Pyridines / chemistry*
Receptors, Nicotinic / chemistry*
Receptors, Nicotinic / metabolism
Silicon
Tomography, Emission-Computed
X-Rays

Substances

Analgesics, Non-Narcotic
Bridged Bicyclo Compounds, Heterocyclic
Pyridines
Receptors, Nicotinic
epibatidine
Silicon