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Synthesis and anti-cancer activity of chiral tetrahydropyrazolo[1,5-a] pyridine-fused steroids

2017-06Journal article Restricted access
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dc.contributor.authorLopes, Susana M. M.
dc.contributor.authorSousa, Emanuel P.
dc.contributor.authorBarreira, Luísa
dc.contributor.authorF. Marques, C.
dc.contributor.authorRodrigues, Maria João
dc.contributor.authorPinho e Melo, Teresa M. V. D.
dc.date.accessioned2019-11-20T15:07:34Z
dc.date.available2019-11-20T15:07:34Z
dc.date.issued2017-06
dc.description.abstractRegio-and stereoselective synthesis of novel chiral 4,5,6,7-tetrahydropyrazolo [1,5-a]pyridine fused steroids via [8 pi + 2 pi] cycloaddition of diazafulvenium methides with steroidal scaffolds is reported. The biological evaluation of the new family of hexacyclic steroids as anti-cancer agents was also carried out. Hexacyclic steroids bearing a benzyl group at C-22, derived from 16-dehydropregnenolone and 16-dehydroprogesterone, show considerable cytotoxicity against EL4 (murine T-lymphoma) in contrast with the corresponding C-22-unsubstituted derivatives showing low cytotoxicity. Thus, results indicate that the presence of the benzyl group is important to ensure cytotoxicity.
dc.description.sponsorshipPortuguese Agency for Scientific Research
dc.description.sponsorshipFundactio para a Glenda e a Tecnologia (FCT) [007630 UID/QUI/00313/2013]
dc.description.sponsorshipFCT [SFRH/BPD/84413/2012]
dc.description.sponsorship[COMPETE2020-UE]
dc.description.versioninfo:eu-repo/semantics/publishedVersion
dc.identifier.doi10.1016/j.steroids.2017.03.006
dc.identifier.issn0039-128X
dc.identifier.issn1878-5867
dc.identifier.urihttp://hdl.handle.net/10400.1/13108
dc.language.isoeng
dc.peerreviewedyes
dc.publisherElsevier Science Inc
dc.subjectC-17 pyrazolinyl derivatives
dc.subjectDiazafulvenium methides
dc.subjectProstate-cancer
dc.subjectProliferation
dc.titleSynthesis and anti-cancer activity of chiral tetrahydropyrazolo[1,5-a] pyridine-fused steroids
dc.typejournal article
dspace.entity.typePublication
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/SFRH/SFRH%2FBPD%2F84413%2F2012/PT
oaire.citation.endPage23
oaire.citation.startPage16
oaire.citation.titleSteroids
oaire.citation.volume122
oaire.fundingStreamSFRH
person.familyNameBarreira
person.familyNameMarques
person.familyNameRodrigues
person.givenNameLuísa
person.givenNameCátia F.
person.givenNameMaria João
person.identifier2399110
person.identifierR-004-VNG
person.identifier.ciencia-id6D1A-17E5-1400
person.identifier.ciencia-id021E-BE70-4712
person.identifier.ciencia-id2514-0E17-1D8D
person.identifier.orcid0000-0002-4077-855X
person.identifier.orcid0000-0002-2955-5304
person.identifier.orcid0000-0001-8732-710X
person.identifier.ridS-6768-2017
person.identifier.scopus-author-id57192868264
person.identifier.scopus-author-id56031608100
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsrestrictedAccess
rcaap.typearticle
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