Synthesis and Biological Evaluation of a New Family of Constrained Azabicyclic Homocholine Analogues

Jill I. Halliday; Mary Chebib; Malcolm D. McLeod

doi:10.1071/CH10024

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Synthesis and Biological Evaluation of a New Family of Constrained Azabicyclic Homocholine Analogues

Jill I. Halliday ^A , Mary Chebib ^B and Malcolm D. McLeod ^C ^D

+ Author Affiliations

- Author Affiliations

^A School of Chemistry, F11, University of Sydney, NSW 2006, Australia.

^B Faculty of Pharmacy, A15, University of Sydney, NSW 2006, Australia.

^C Research School of Chemistry, Australian National University, Canberra, ACT 0200, Australia.

^D Corresponding author. Email: malcolm.mcleod@anu.edu.au

Australian Journal of Chemistry 63(5) 808-812 https://doi.org/10.1071/CH10024
Submitted: 14 January 2010 Accepted: 11 February 2010 Published: 21 May 2010

Abstract

A family of constrained acylated homocholine analogues have been synthesized, based on the azabicyclic ring scaffold derived from a double-Mannich annulation of cyclic ketones. The short synthetic route allows generation of structural diversity including, variation in the carbocyclic ring size, bridgehead substitution, nitrogen substitution and the ester sidechain. Biological assays on selected analogues demonstrate these compounds are nicotinic acetylcholine receptor (nAChR) antagonists. Several analogues also bind to other neuronal transporter and receptor targets.

Acknowledgements

We thank The Australian National University, The University of Sydney and the Australian Research Council Discovery Project Scheme (DP0663006) for supporting this work.

References

Synthesis and Biological Evaluation of a New Family of Constrained Azabicyclic Homocholine Analogues

Abstract

Acknowledgements

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