Conformationally constrained nicotines: polycyclic, bridged, and spiro-annulated analogues as novel ligands for the nicotinic acetylcholine receptor

T Ullrich, S Krich, D Binder, K Mereiter…

Index: Ullrich, Thomas; Krich, Sylvia; Binder, Dieter; Mereiter, Kurt; Anderson, David J.; Meyer, Michael D.; Pyerin, Michael Journal of Medicinal Chemistry, 2002 , vol. 45, # 18 p. 4047 - 4054

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Citation Number: 31

Abstract

A set of novel nicotine-related, conformationally constrained compounds, including tetracyclic, bridged (4), and tricyclic, spiro-annulated (5) structures, were synthesized in a straightforward manner and optically resolved in a convenient fashion with (+)-and (-)-O, O'- di-p-toluoyltartaric acids. Absolute configurations were determined by X-ray crystallography. These compounds were evaluated for their ability to displace [3H] cytisine in a rat ...