Show simple item record

dc.contributor.authorButler, Nicholas M
dc.contributor.authorHendra, Rudi
dc.contributor.authorBremner, John B
dc.contributor.authorWillis, Anthony C
dc.contributor.authorLucantoni, Leonardo
dc.contributor.authorAvery, Vicky M
dc.contributor.authorKeller, Paul A
dc.date.accessioned2019-05-29T13:16:12Z
dc.date.available2019-05-29T13:16:12Z
dc.date.issued2018
dc.identifier.issn1477-0520
dc.identifier.doi10.1039/C8OB00865E
dc.identifier.urihttp://hdl.handle.net/10072/382125
dc.description.abstractThe base-initiated alkylation of the abundant natural dye indigo 1 with ring-strained electrophiles results in the unprecedented, one-pot synthesis of functionalised dihydropyrazino[1,2-a:4,3-a′]diindoles, dihydroepoxy[1,5]oxazocino[5,4-a:3,2-b′]diindoles, and dihydrodiazepino[1,2-a:4,3-a′]diindoles, resulting from intramolecular ring opening-expansion cyclisation processes of their parent oxiranes and aziridines. Regiochemical and stereochemical aspects of the reactions are reported together with integrated mechanistic proposals. This new indigo cascade chemistry should have broad applicability in the synthesis of chemical architectures, not readily-accessible by other means. The three-step synthesis of the useful synthetic precursor (R)-2-(chloromethyl)-1-tosylaziridine 14 is also described. Initial biological activity investigations into these new 2,2′-dindolyl-based heterocyclic derivatives revealed potent, selective antiplasmodial activity in vitro for several isolated structures, with IC50 values as low as 76.6 nM for (±)-8, while demonstrating low human cell toxicity.
dc.description.peerreviewedYes
dc.languageEnglish
dc.language.isoeng
dc.publisherRSC Publishing
dc.publisher.placeUnited Kingdom
dc.relation.ispartofpagefrom6006
dc.relation.ispartofpageto6016
dc.relation.ispartofissue33
dc.relation.ispartofjournalOrganic and Biomolecular Chemistry
dc.relation.ispartofvolume16
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchMedicinal and biomolecular chemistry not elsewhere classified
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode340499
dc.subject.fieldofresearchcode3405
dc.titleCascade reactions of indigo with oxiranes and aziridines: efficient access to dihydropyrazinodiindoles and spiro-oxazocinodiindoles
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.hasfulltextNo Full Text
gro.griffith.authorAvery, Vicky M.


Files in this item

FilesSizeFormatView

There are no files associated with this item.

This item appears in the following Collection(s)

  • Journal articles
    Contains articles published by Griffith authors in scholarly journals.

Show simple item record