Asymmetric total synthesis and antiproliferative activity of goniothalamin oxide isomers

dc.creatorMarquissolo, C
dc.creatorde Fatima, A
dc.creatorKohn, LK
dc.creatorRuiz, ALTG
dc.creatorde Carvalho, JE
dc.creatorPilli, RA
dc.date2009
dc.dateFEB-JUN
dc.date2014-11-17T02:50:01Z
dc.date2015-11-26T16:36:09Z
dc.date2014-11-17T02:50:01Z
dc.date2015-11-26T16:36:09Z
dc.date.accessioned2018-03-28T23:18:47Z
dc.date.available2018-03-28T23:18:47Z
dc.identifierBioorganic Chemistry. Academic Press Inc Elsevier Science, v. 37, n. 41699, n. 52, n. 56, 2009.
dc.identifier0045-2068
dc.identifierWOS:000267396000008
dc.identifier10.1016/j.bioorg.2008.12.001
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/55104
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/55104
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/55104
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1271714
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionGoniothalamin 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 anti proliferative 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. Anti proliferative 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. (C) 2009 Published by Elsevier Inc.
dc.description37
dc.description41699
dc.description52
dc.description56
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionUniversidade Federal de Minas Gerais (UFMG)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.languageen
dc.publisherAcademic Press Inc Elsevier Science
dc.publisherSan Diego
dc.publisherEUA
dc.relationBioorganic Chemistry
dc.relationBioorganic Chem.
dc.rightsfechado
dc.rightshttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dc.sourceWeb of Science
dc.subjectGoniothalamin oxides
dc.subjectEnantiomers
dc.subjectEpoxidation
dc.subjectAntiproliferative activity
dc.subjectCancer cells
dc.subjectStyryl-lactones
dc.subjectCancer-cells
dc.subject(r)-argentilactone
dc.subjectDerivatives
dc.subject(r)-goniothalamin
dc.subjectEpoxidation
dc.subjectEnantiomers
dc.subjectLines
dc.titleAsymmetric total synthesis and antiproliferative activity of goniothalamin oxide isomers
dc.typeArtículos de revistas


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