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Synthesis of thioridazine-VLA-4 antagonist hybrids using N-propargyl northioridazine enantiomers

Martyn, A. P.; Willis, Anthony; Kelso, Michael

Description

Herein, we report the synthesis of thioridazine-VLA-4 hybrid epimers. These hybrid molecules were obtained by means of a click reaction involving N-propargyl northioridazine enantiomers and an azide containing VLA-4 antagonist. A synthesis of northioridazine enantiomers from racemic thioridazine was developed and the absolute stereochemistry was confirmed by X-ray crystallography. Access to N-substituted thioridazine analogs may reveal that this phenothiazine core has therapeutic potential in...[Show more]

dc.contributor.authorMartyn, A. P.
dc.contributor.authorWillis, Anthony
dc.contributor.authorKelso, Michael
dc.date.accessioned2022-07-26T23:43:19Z
dc.identifier.issn0039-7911
dc.identifier.urihttp://hdl.handle.net/1885/269947
dc.description.abstractHerein, we report the synthesis of thioridazine-VLA-4 hybrid epimers. These hybrid molecules were obtained by means of a click reaction involving N-propargyl northioridazine enantiomers and an azide containing VLA-4 antagonist. A synthesis of northioridazine enantiomers from racemic thioridazine was developed and the absolute stereochemistry was confirmed by X-ray crystallography. Access to N-substituted thioridazine analogs may reveal that this phenothiazine core has therapeutic potential in other disease avenues.
dc.description.sponsorshipThis study was supported by the Arrow Bone Marrow Transplant Foundation for their financial support with an Arrow HCC PhD Scholarship.
dc.format.mimetypeapplication/pdf
dc.language.isoen_AU
dc.publisherTaylor & Francis Group
dc.rights© 2020 Taylor & Francis Group, LLC
dc.sourceSynthetic Communications
dc.subjectClick
dc.subjectnorthioridazine
dc.subjectthioridazine
dc.subjectVLA-4
dc.titleSynthesis of thioridazine-VLA-4 antagonist hybrids using N-propargyl northioridazine enantiomers
dc.typeJournal article
local.description.notesImported from ARIES
local.identifier.citationvolume50
dc.date.issued2020
local.identifier.absfor349999 - Other chemical sciences not elsewhere classified
local.identifier.ariespublicationa383154xPUB14784
local.publisher.urlhttps://www.routledge.com/
local.type.statusPublished Version
local.contributor.affiliationMartyn, A. P., University of Wollongong
local.contributor.affiliationWillis, Anthony, College of Science, ANU
local.contributor.affiliationKelso, Michael, University of Wollongong
local.description.embargo2099-12-31
local.bibliographicCitation.issue18
local.bibliographicCitation.startpage2796
local.bibliographicCitation.lastpage2809
local.identifier.doi10.1080/00397911.2020.1785503
dc.date.updated2021-08-01T08:24:00Z
local.identifier.scopusID2-s2.0-85087633831
CollectionsANU Research Publications

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