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Synthesis of ABC Analogues of the Antitumour Antibiotic Streptonigrin

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dc.contributor.authorKimber, Marc C
dc.contributor.authorAnderberg, Pia I
dc.contributor.authorHarding, Margaret
dc.date.accessioned2015-12-13T22:26:25Z
dc.date.issued2000
dc.date.updated2015-12-11T08:22:11Z
dc.description.abstractABC analogues of the antitumour antibiotic streptonigrin, that contain the key metal chelation site and redox-active quinone unit that are essential for biological activity, were prepared via palladium catalysed cross-coupling of 2-iodo-8-nitroquinoline or 2-iodo-6-methoxy-5-nitroquinoline with 2- trimethylstannio-6-methylpyridine. Mild oxidation of the pyridyl methyl group introduced the acid functional group on ring C and Fremy's salt oxidation afforded the quinone unit which was elaborated to give the 5-amino-6-methoxy substitution pattern present in streptonigrin. 2000 Elsevier Science Ltd.
dc.identifier.issn0040-4020
dc.identifier.urihttp://hdl.handle.net/1885/73506
dc.publisherElsevier
dc.sourceTetrahedron
dc.source.urihttp://ac.els-cdn.com/S0040402000002672/1-s2.0-S0040402000002672-main.pdf?_tid=e2857120-fd65-11e2-a25c-00000aab0f6b&acdnat=1375662661_1dd8cc26912b206ac99118f45ff9f6e5
dc.subjectKeywords: antineoplastic antibiotic; palladium complex; rufocromomycin; rufocromomycin derivative; unclassified drug; article; catalyst; drug structure; drug synthesis; oxidation; priority journal; structure activity relation; structure analysis Antitumour compounds; Bicyclic heterocyclic compounds; Coupling reactions; Quinolinones
dc.titleSynthesis of ABC Analogues of the Antitumour Antibiotic Streptonigrin
dc.typeJournal article
local.bibliographicCitation.issue22
local.bibliographicCitation.lastpage3581
local.bibliographicCitation.startpage3575
local.contributor.affiliationKimber, Marc C, University of Sydney
local.contributor.affiliationAnderberg, Pia I, University of Sydney
local.contributor.affiliationHarding, Margaret, Administrative Division, ANU
local.contributor.authoruidHarding, Margaret, u4044881
local.description.embargo2037-12-31
local.description.notesImported from ARIES
local.identifier.absfor030500 - ORGANIC CHEMISTRY
local.identifier.ariespublicationf5625xPUB3719
local.identifier.citationvolume56
local.identifier.scopusID2-s2.0-0034717128
local.type.statusPublished Version

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