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dc.contributor.CRUESPUNIVERSIDADE DE ESTADUAL DE CAMPINASpt_BR
dc.typeArtigo de periódicopt_BR
dc.titleAsymmetric Total Synthesis And Antiproliferative Activity Of Goniothalamin Oxide Isomers.pt_BR
dc.contributor.authorMarquissolo, Cilenept_BR
dc.contributor.authorde Fátima, Angelopt_BR
dc.contributor.authorKohn, Luciana Kpt_BR
dc.contributor.authorRuiz, Ana Lúcia T Gpt_BR
dc.contributor.authorde Carvalho, João Ernestopt_BR
dc.contributor.authorPilli, Ronaldo Apt_BR
unicamp.authorCilene Marquissolo, Departamento de Química Orgânica, Instituto de Química, Universidade Estadual de Campinas, CP 6154, Campinas, SP 13083-970, Brazil.pt_BR
unicamp.author.externalAngelo de Fátima,pt
unicamp.author.externalLuciana K Kohn,pt
unicamp.author.externalAna Lúcia T G Ruiz,pt
unicamp.author.externalJoão Ernesto de Carvalho,pt
unicamp.author.externalRonaldo A Pilli,pt
dc.subjectAntineoplastic Agentspt_BR
dc.subjectCatalysispt_BR
dc.subjectCell Line, Tumorpt_BR
dc.subjectChlorobenzoatespt_BR
dc.subjectDrug Screening Assays, Antitumorpt_BR
dc.subjectEpoxy Compoundspt_BR
dc.subjectHumanspt_BR
dc.subjectPyronespt_BR
dc.subjectStereoisomerismpt_BR
dc.description.abstractGoniothalamin oxide (1) is a styryl lactone which was isolated from bark and leaves of several Goniothalamus species. This natural product has some interesting biological properties such as larvicidal and tripanocidal activities. However, no studies on the antiproliferative profile of goniothalamin oxide (1) and its stereoisomers have been reported yet. Here, goniothalamin epoxide (1), isogoniothalamin epoxide (2) and their enantiomers were prepared via epoxidation of (R)-and (S)-goniothalamin (4). A 3:2 molar ratio in favor of goniothalamin oxide (1) and ent-1 was observed from (R)- and (S)-4, respectively, when 3-chloroperbenzoic acid (mCPBA) was employed while an increase to 6:1 molar ratio was achieved with (S,S)-Jacobsen's catalyst. Antiproliferative activity of these epoxides revealed that ent-isogoniothalamin oxide (ent-2) was the most active against the eight cancer cell lines studied. These results indicate that 6S, 7R and 8R absolute configurations are beneficial for the activity of these epoxides.en
dc.relation.ispartofBioorganic Chemistrypt_BR
dc.relation.ispartofabbreviationBioorg. Chem.pt_BR
dc.date.issued2009-Aprpt_BR
dc.identifier.citationBioorganic Chemistry. v. 37, n. 2, p. 52-6, 2009-Apr.pt_BR
dc.language.isoengpt_BR
dc.description.volume37pt_BR
dc.description.firstpage52-6pt_BR
dc.rightsfechadopt_BR
dc.sourcePubMedpt_BR
dc.identifier.issn1090-2120pt_BR
dc.identifier.doi10.1016/j.bioorg.2008.12.001pt_BR
dc.identifier.urlhttp://www.ncbi.nlm.nih.gov/pubmed/19185327pt_BR
dc.date.available2015-11-27T13:15:57Z-
dc.date.accessioned2015-11-27T13:15:57Z-
dc.description.provenanceMade available in DSpace on 2015-11-27T13:15:57Z (GMT). No. of bitstreams: 1 pmed_19185327.pdf: 342392 bytes, checksum: a5b98bf4a87bc12b4d25a711108f1992 (MD5) Previous issue date: 2009en
dc.identifier.urihttp://repositorio.unicamp.br/jspui/handle/REPOSIP/198663-
dc.identifier.idPubmed19185327pt_BR
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