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dc.contributorSistema FMUSP-HC: Faculdade de Medicina da Universidade de São Paulo (FMUSP) e Hospital das Clínicas da FMUSP
dc.contributor.authorPIEPER, Pauline
dc.contributor.authorMCHUGH, Eliza
dc.contributor.authorAMARAL, Maiara
dc.contributor.authorTEMPONE, Andre G.
dc.contributor.authorANDERSON, Edward A.
dc.date.accessioned2020-03-24T15:16:32Z-
dc.date.available2020-03-24T15:16:32Z-
dc.date.issued2020
dc.identifier.citationTETRAHEDRON, v.76, n.2, Special Issue, article ID 130814, 8p, 2020
dc.identifier.issn0040-4020
dc.identifier.urihttps://observatorio.fm.usp.br/handle/OPI/35727-
dc.description.abstractChagas disease and visceral leishmaniasis are neglected protozoan diseases with significant impact in developing countries. Due to the limited number and toxicity of current therapies, new drug leads are urgently needed. In this work, four aporphine natural products were synthesized using an enantioselective, modular and convergent strategy, comprising eight steps in the longest linear sequence; key steps included Bischler-Napieralski cyclization/Noyori asymmetric reduction to construct the tetrahydroisoquinolines, and palladium-catalyzed arylation to close the C ring. Norglaucine, nordicentrine and dicentrine showed promising bioactivity against T. cruzi and L. infantum, suggesting potential for further development of these scaffolds as antiparasitic agents.eng
dc.description.sponsorshipSwiss National Science FoundationSwiss National Science Foundation (SNSF)
dc.description.sponsorshipMarie Sklodowska-Curie actions for an Individual Fellowship [832700]
dc.description.sponsorshipOxford Internal GCRF Research England Fund [0006019]
dc.description.sponsorshipEPSRCEngineering & Physical Sciences Research Council (EPSRC) [EP/M019195/1]
dc.description.sponsorshipSao Paulo State Research FoundationFundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP) [FAPESP 2018/10279-6, 2018/25128-3]
dc.description.sponsorshipConselho Nacional de Pesquisa e DesenvolvimentoNational Council for Scientific and Technological Development (CNPq)
dc.language.isoeng
dc.publisherPERGAMON-ELSEVIER SCIENCE LTDeng
dc.relation.ispartofTetrahedron
dc.rightsrestrictedAccesseng
dc.subjectNatural productseng
dc.subjectAporphineeng
dc.subjectLeishmania infantumeng
dc.subjectTrypanosoma cruzieng
dc.subjectAlkaloideng
dc.subjectPalladium catalyzed arylationeng
dc.subject.otheralkaloidseng
dc.subject.otherleishmaniaeng
dc.subject.otherhydrogenationeng
dc.subject.otherisoquinolineeng
dc.subject.otherglaucineeng
dc.titleEnantioselective synthesis and anti-parasitic properties of aporphine natural productseng
dc.typearticleeng
dc.rights.holderCopyright PERGAMON-ELSEVIER SCIENCE LTDeng
dc.identifier.doi10.1016/j.tet.2019.130814
dc.subject.wosChemistry, Organiceng
dc.type.categoryoriginal articleeng
dc.type.versionpublishedVersioneng
hcfmusp.author.externalPIEPER, Pauline:Univ Oxford, Chem Res Lab, 12 Mansfield Rd, Oxford OX1 3TA, England
hcfmusp.author.externalMCHUGH, Eliza:Univ Oxford, Chem Res Lab, 12 Mansfield Rd, Oxford OX1 3TA, England
hcfmusp.author.externalTEMPONE, Andre G.:Adolfo Lutz Inst, Ctr Parasitol & Mycol, Av Dr Arnaldo 351, BR-01246000 Sao Paulo, Brazil
hcfmusp.author.externalANDERSON, Edward A.:Univ Oxford, Chem Res Lab, 12 Mansfield Rd, Oxford OX1 3TA, England
hcfmusp.description.articlenumber130814
hcfmusp.description.issue2
hcfmusp.description.issueSpecial Issue
hcfmusp.description.volume76
hcfmusp.origemWOS
hcfmusp.origem.idWOS:000508749800004
hcfmusp.origem.id2-s2.0-85075865363
hcfmusp.publisher.cityOXFORDeng
hcfmusp.publisher.countryENGLANDeng
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dc.description.indexPubMedeng
hcfmusp.citation.scopus12-
hcfmusp.scopus.lastupdate2022-06-03-
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