Levoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as Scaffolds for Drug Discovery and Development

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dc.contributor.authorLiu, Xin
dc.contributor.authorCarr, Paul D
dc.contributor.authorGardiner, Michael
dc.contributor.authorBanwell, Martin
dc.contributor.authorElbanna, Ahmed H
dc.contributor.authorKhalil, Zeinab G
dc.contributor.authorCapon, Robert J
dc.date.accessioned2022-07-13T01:40:14Z
dc.date.available2022-07-13T01:40:14Z
dc.date.issued2020
dc.date.updated2021-08-01T08:22:26Z
dc.description.abstractThe bioderived platform molecule levoglucosenone (LGO, 1) and its readily prepared pseudoenantiomer (iso-LGO, 2) have each been subjected to α-iodination reactions with the product halides then being engaged in palladium-catalyzed Ullmann cross-coupling reactions with various bromonitropyridines. The corresponding α-pyridinylated derivatives such as 11 and 24, respectively, are produced as a result. Biological screening of such products reveals that certain of them display potent and selective antimicrobial and/or cytotoxic properties. In contrast, the azaindoles obtained by reductive cyclization of compounds such as 11 and 12 are essentially inactive in these respects. Preliminary mode-of-action studies are reporteden_AU
dc.description.sponsorshipFunding from the Australian Research Council is also acknowledgeden_AU
dc.format.mimetypeapplication/pdfen_AU
dc.identifier.issn2470-1343en_AU
dc.identifier.urihttp://hdl.handle.net/1885/268820
dc.language.isoen_AUen_AU
dc.provenanceThis is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.en_AU
dc.publisherACS Publicationsen_AU
dc.rights© 2020 American Chemical Societyen_AU
dc.rights.licenseACS AuthorChoice Licenseen_AU
dc.rights.urihttps://pubs.acs.org/page/policy/authorchoice_termsofuse.htmlen_AU
dc.sourceACS Omegaen_AU
dc.titleLevoglucosenone and Its Pseudoenantiomer iso-Levoglucosenone as Scaffolds for Drug Discovery and Developmenten_AU
dc.typeJournal articleen_AU
dcterms.accessRightsOpen Accessen_AU
local.bibliographicCitation.issue23en_AU
local.bibliographicCitation.lastpage13939en_AU
local.bibliographicCitation.startpage13926en_AU
local.contributor.affiliationLiu, Xin, College of Science, ANUen_AU
local.contributor.affiliationCarr, Paul D, College of Science, ANUen_AU
local.contributor.affiliationGardiner, Michael, College of Science, ANUen_AU
local.contributor.affiliationBanwell, Martin, College of Science, ANUen_AU
local.contributor.affiliationElbanna, Ahmed H, University of Queenslanden_AU
local.contributor.affiliationKhalil, Zeinab G, University of Queenslanden_AU
local.contributor.affiliationCapon, Robert J, University of Queenslanden_AU
local.contributor.authoremailu1072089@anu.edu.auen_AU
local.contributor.authoruidLiu, Xin, u6180982en_AU
local.contributor.authoruidCarr, Paul D, u9206448en_AU
local.contributor.authoruidGardiner, Michael, u1072089en_AU
local.contributor.authoruidBanwell, Martin, u9500594en_AU
local.description.notesImported from ARIESen_AU
local.identifier.absfor000000 - Internal ANU use onlyen_AU
local.identifier.ariespublicationa383154xPUB13401en_AU
local.identifier.citationvolume5en_AU
local.identifier.doi10.1021/acsomega.0c01331en_AU
local.identifier.scopusID2-s2.0-85087468387
local.identifier.uidSubmittedBya383154en_AU
local.publisher.urlhttp://pubs.acs.org/journal/acsodfen_AU
local.type.statusPublished Versionen_AU

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