Long-chain triazolyl acids as inhibitors of osteoclastogenesis

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dc.contributor.author Marshall, Andrew en
dc.contributor.author Lin, Jianming en
dc.contributor.author Grey, Andrew en
dc.contributor.author Reid, Ian en
dc.contributor.author Cornish, Jillian en
dc.contributor.author Denny, William en
dc.date.accessioned 2016-10-06T01:04:35Z en
dc.date.issued 2013-07-15 en
dc.identifier.citation Bioorganic and Medicinal Chemistry, 2013, 21 (14), pp. 4112 - 4119 en
dc.identifier.issn 0968-0896 en
dc.identifier.uri http://hdl.handle.net/2292/30637 en
dc.description.abstract Saturated fatty acids (e.g., palmitic acid) are known to moderately inhibit the development of osteoclasts in vitro. In pursuit of more effective inhibitors of osteoclastogenesis we explored two new classes of palmitic acid analogues containing either an ether or triazolyl group at various positions along the chain. The compounds were evaluated for their ability to inhibit the formation of osteoclasts in primary mouse bone marrow cultures. The oxyacids were generally prepared by condensation of the appropriate alkyl halides and diols, followed by Jones oxidation. The triazolyl acids were prepared by copper-catalysed click chemistry between alkyl azides and acetylenic acids, or with the appropriately-protected azides and alkynes, followed by deprotection and oxidation. The oxyacids were little more effective than palmitic acid, but the triazolyl analogues were much more effective osteoclastogenesis inhibitors, especially when the triazole was distant from the acid unit. en
dc.description.uri http://www.journals.elsevier.com/bioorganic-and-medicinal-chemistry/ en
dc.publisher Elsevier en
dc.relation.ispartofseries Bioorganic and Medicinal Chemistry en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/0968-0896/ en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.title Long-chain triazolyl acids as inhibitors of osteoclastogenesis en
dc.type Journal Article en
dc.identifier.doi 10.1016/j.bmc.2013.05.013 en
pubs.issue 14 en
pubs.begin-page 4112 en
pubs.volume 21 en
dc.rights.holder Copyright: Elsevier en
dc.identifier.pmid 23726411 en
pubs.author-url http://www.sciencedirect.com/science/article/pii/S0968089613004380 en
pubs.end-page 4119 en
pubs.publication-status Published en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 400248 en
pubs.org-id Medical and Health Sciences en
pubs.org-id Medical Sciences en
pubs.org-id Auckland Cancer Research en
pubs.org-id School of Medicine en
pubs.org-id Medicine Department en
pubs.org-id Science en
pubs.org-id Science Research en
pubs.org-id Maurice Wilkins Centre (2010-2014) en
dc.identifier.eissn 1464-3391 en
pubs.record-created-at-source-date 2016-10-06 en
pubs.dimensions-id 23726411 en

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