Synthesis of stemofoline analogues as acetylcholinesterase inhibitors

Sastraruji, K; Sastraruji, T; Ung, AT; Griffith, R; Jatisatienr, A; Pyne, SG

Synthesis of stemofoline analogues as acetylcholinesterase inhibitors

Sastraruji, K Sastraruji, T Ung, AT

Griffith, R Jatisatienr, A Pyne, SG

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Publication Type:: Journal Article
Citation:: Tetrahedron, 2012, 68 (35), pp. 7103 - 7115
Issue Date:: 2012-09-02

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Field	Value	Language
dc.contributor.author	Sastraruji, K	en_US
dc.contributor.author	Sastraruji, T	en_US
dc.contributor.author	Ung, AT https://orcid.org/0000-0002-5665-0702	en_US
dc.contributor.author	Griffith, R	en_US
dc.contributor.author	Jatisatienr, A	en_US
dc.contributor.author	Pyne, SG	en_US
dc.date.issued	2012-09-02	en_US
dc.identifier.citation	Tetrahedron, 2012, 68 (35), pp. 7103 - 7115	en_US
dc.identifier.issn	0040-4020	en_US
dc.identifier.uri	http://hdl.handle.net/10453/17989
dc.description.abstract	Thirty-two new stemofoline analogues were prepared from didehydrostemofoline for studies as AChE inhibitors. C-3 Side-chain modified amino, carbamate, triazole and oxazole stemofoline derivatives were prepared. In general the amine derivatives were found to be stronger inhibitors of AChE than their alcohol analogues that we previously reported. Compounds 5 and 26, with small C-3 side-chain substituents, were two of the most active inhibitors. Preliminary molecular docking studies suggested that these compounds may inhibit AChE by binding horizontally along the passage of the active-site gorge and block access to acetylcholine. © 2012 Elsevier Ltd. All rights reserved.	en_US
dc.relation.ispartof	Tetrahedron	en_US
dc.relation.isbasedon	10.1016/j.tet.2012.06.047	en_US
dc.subject.classification	Organic Chemistry	en_US
dc.title	Synthesis of stemofoline analogues as acetylcholinesterase inhibitors	en_US
dc.type	Journal Article
utslib.citation.volume	35	en_US
utslib.citation.volume	68	en_US
utslib.for	0305 Organic Chemistry	en_US
utslib.for	0304 Medicinal and Biomolecular Chemistry	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	closed_access
pubs.issue	35	en_US
pubs.publication-status	Published	en_US
pubs.volume	68	en_US

Abstract:

Thirty-two new stemofoline analogues were prepared from didehydrostemofoline for studies as AChE inhibitors. C-3 Side-chain modified amino, carbamate, triazole and oxazole stemofoline derivatives were prepared. In general the amine derivatives were found to be stronger inhibitors of AChE than their alcohol analogues that we previously reported. Compounds 5 and 26, with small C-3 side-chain substituents, were two of the most active inhibitors. Preliminary molecular docking studies suggested that these compounds may inhibit AChE by binding horizontally along the passage of the active-site gorge and block access to acetylcholine. © 2012 Elsevier Ltd. All rights reserved.

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http://hdl.handle.net/10453/17989