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Synthesis and biological evaluation of a new family of constrained azabicyclic homocholine analogues

Halliday, Jill I; Chebib, Mary; McLeod, Malcolm

Description

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....[Show more]

dc.contributor.authorHalliday, Jill I
dc.contributor.authorChebib, Mary
dc.contributor.authorMcLeod, Malcolm
dc.date.accessioned2015-12-07T22:47:44Z
dc.identifier.issn0004-9425
dc.identifier.urihttp://hdl.handle.net/1885/26176
dc.description.abstractA 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.
dc.publisherCSIRO Publishing
dc.sourceAustralian Journal of Chemistry
dc.subjectKeywords: Azabicyclic ring; Biological assays; Biological evaluation; Carbocyclic rings; Cyclic ketones; Nicotinic acetylcholine receptors (nAChR); Receptor targets; Side-chain; Structural diversity; Synthetic routes; Esters; Ketones; Synthesis (chemical)
dc.titleSynthesis and biological evaluation of a new family of constrained azabicyclic homocholine analogues
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume63
dc.date.issued2010
local.identifier.absfor030499 - Medicinal and Biomolecular Chemistry not elsewhere classified
local.identifier.ariespublicationu2544221xPUB43
local.type.statusPublished Version
local.contributor.affiliationHalliday, Jill I, University of Sydney
local.contributor.affiliationChebib, Mary, University of Sydney
local.contributor.affiliationMcLeod, Malcolm, College of Physical and Mathematical Sciences, ANU
local.description.embargo2037-12-31
local.bibliographicCitation.issue5
local.bibliographicCitation.startpage808
local.bibliographicCitation.lastpage812
local.identifier.doi10.1071/CH10024
local.identifier.absseo970103 - Expanding Knowledge in the Chemical Sciences
dc.date.updated2016-02-24T09:51:32Z
local.identifier.scopusID2-s2.0-77953015801
local.identifier.thomsonID000277891900011
CollectionsANU Research Publications

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