Issue 22, 2003
From the journal:

Organic & Biomolecular Chemistry

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

Zhi-Liang Wei,a   Yingxian Xiao,b   Clifford George,c   Kenneth J. Kellarb  and  Alan P. Kozikowski*a  

* Corresponding authors

a Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 S. Wood Street, Chicago, Illinois, USA
E-mail: kozikowa@uic.edu
Fax: +1-312-996-7107
Tel: +1-312-996-5972

b Department of Pharmacology, Georgetown University, 3900 Reservoir Road, NW Washington DC, USA

c Naval Research Laboratory, 4555 Overlook Avenue, SW Washington DC, USA

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.

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

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Article information

DOI
https://doi.org/10.1039/B308906A
Article type
Communication
Submitted
30 Jul 2003
Accepted
23 Sep 2003
First published
10 Oct 2003

Org. Biomol. Chem., 2003,1, 3878-3881

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

Z. Wei, Y. Xiao, C. George, K. J. Kellar and A. P. Kozikowski, Org. Biomol. Chem., 2003, 1, 3878 DOI: 10.1039/B308906A

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