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Diels–alder/thiol–olefin co-oxygenation approach to antimalarials incorporating the 2,3-dioxabicyclo[3.3.1]nonane pharmacophore

2006Journal article Restricted access
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dc.contributor.authorO'Neill, Paul M.
dc.contributor.authorVerissimo, Edite
dc.contributor.authorWard, Stephen A.
dc.contributor.authorDavies, Jill
dc.contributor.authorKorshin, Edward E.
dc.contributor.authorAraujo, Nuna C. P.
dc.contributor.authorPugh, Matthew D.
dc.contributor.authorCristiano, Maria Lurdes Santos
dc.contributor.authorStocks, Paul A.
dc.contributor.authorBachi, Mario D.
dc.date.accessioned2014-06-09T14:16:01Z
dc.date.available2014-06-09T14:16:01Z
dc.date.issued2006
dc.date.updated2014-06-05T10:19:44Z
dc.description.abstractAbstract—A Diels–Alder/thiol–olefin co-oxygenation approach to the synthesis of novel bicyclic endoperoxides 17a–22b is reported. Some of these endoperoxides (e.g., 17b, 19b, 22a and 22b) have potent nanomolar in vitro antimalarial activity equivalent to that of the synthetic antimalarial agent arteflene. Iron(II)-mediated degradation of sulfone-endoperoxide 19b and spin-trapping with TEMPO provide a spin-trapped adduct 25 indicative of the formation of a secondary carbon centered radical species 24. Reactive C-radical intermediates of this type may be involved in the expression of the antimalarial effect of these bicyclic endoperoxides.por
dc.identifier.citationO’Neill, Paul M.; Verissimo, Edite; Ward, Stephen A.; Davies, Jill; Korshin, Edward E.; Araujo, Nuna; Pugh, Matthew D.; Cristiano, M. Lurdes S.; Stocks, Paul A.; Bachi, Mario D. Diels–Alder/thiol–olefin co-oxygenation approach to antimalarials incorporating the 2,3-dioxabicyclo[3.3.1]nonane pharmacophore, Bioorganic & Medicinal Chemistry Letters, 16, 11, 2991-2995, 2006.por
dc.identifier.doihttp://dx.doi.org/10.1016/j.bmcl.2006.02.059
dc.identifier.issn0960-894X
dc.identifier.otherAUT: MCR00716;
dc.identifier.urihttp://hdl.handle.net/10400.1/4260
dc.language.isoengpor
dc.peerreviewedyespor
dc.publisherElsevierpor
dc.titleDiels–alder/thiol–olefin co-oxygenation approach to antimalarials incorporating the 2,3-dioxabicyclo[3.3.1]nonane pharmacophorepor
dc.typejournal article
dspace.entity.typePublication
oaire.citation.endPage2995por
oaire.citation.issue11por
oaire.citation.startPage2991por
oaire.citation.titleBioorganic & Medicinal Chemistry Letterspor
oaire.citation.volume16por
person.familyNameAraujo
person.familyNameCristiano
person.givenNameNuna
person.givenNameMaria de Lurdes
person.identifier.ciencia-idE411-6006-5A01
person.identifier.orcid0000-0002-7602-0150
person.identifier.orcid0000-0002-9447-2855
person.identifier.ridN-8531-2013
person.identifier.ridG-2345-2012
person.identifier.scopus-author-id9238724800
rcaap.rightsrestrictedAccesspor
rcaap.typearticlepor
relation.isAuthorOfPublication3423e71b-934d-4da7-9c81-4e56c7930252
relation.isAuthorOfPublicationb16751a6-748e-44b0-9c59-058cbd5b2cc3
relation.isAuthorOfPublication.latestForDiscovery3423e71b-934d-4da7-9c81-4e56c7930252

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