Synthesis of methoxylated goniothalamin, aza-goniothalamin and gamma-pyrones and their in vitro evaluation against human cancer cells

dc.creatorBarcelos, RC
dc.creatorPastre, JC
dc.creatorCaixeta, V
dc.creatorVendramini-Costa, DB
dc.creatorde Carvalho, JE
dc.creatorPilli, RA
dc.date2012
dc.date37043
dc.date2014-08-01T18:27:33Z
dc.date2015-11-26T16:28:27Z
dc.date2014-08-01T18:27:33Z
dc.date2015-11-26T16:28:27Z
dc.date.accessioned2018-03-28T23:09:28Z
dc.date.available2018-03-28T23:09:28Z
dc.identifierBioorganic & Medicinal Chemistry. Pergamon-elsevier Science Ltd, v. 20, n. 11, n. 3635, n. 3651, 2012.
dc.identifier0968-0896
dc.identifierWOS:000303935800026
dc.identifier10.1016/j.bmc.2012.03.059
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/79244
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/79244
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1269469
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.descriptionThe present work describes the preparation of three novel series of compounds based on the structure of goniothalamin, a natural styryl lactone which has been found to display cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 29 novel goniothalamin analogues was prepared and evaluated against seven human cancer cell lines. While the gamma-pyrones and the azagoniothalamin analogues were less potent than the lead compound, 2,4-dimethoxy analogue 88 has shown to be more potent in vitro than goniothalamin against all cancer cell lines evaluated. Furthermore, it was more potent than doxorubicin against NCI-ADR/RES, OVCAR-03 and HT-29 while being less toxic to human keratinocytes (HaCat). The 3,5-dimethoxy analogue 90 and 2,4,5-trimethoxy analogue 92 also displayed promising antiproliferative activity when compared to goniothalamin ( 1). These results provide new elements for the design and synthesis of novel representatives of this family of natural compounds. (C) 2012 Elsevier Ltd. All rights reserved.
dc.description20
dc.description11
dc.description3635
dc.description3651
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)
dc.descriptionFAPESP [10/16990-1, 2009/51602-5]
dc.languageen
dc.publisherPergamon-elsevier Science Ltd
dc.publisherOxford
dc.publisherInglaterra
dc.relationBioorganic & Medicinal Chemistry
dc.relationBioorg. Med. Chem.
dc.rightsfechado
dc.rightshttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dc.sourceWeb of Science
dc.subjectGoniothalamin
dc.subjectCancer cells
dc.subjectAntiproliferative activity
dc.subjectgamma-Pyrones
dc.subjectDihydro-gamma-pyrones
dc.subjectAza-goniothalamin
dc.subjectStyryl-lactone Goniothalamin
dc.subjectAnticancer Drug Screen
dc.subjectCytotoxic Activity
dc.subjectNatural-products
dc.subjectTumor
dc.subjectEnantiomers
dc.subjectApoptosis
dc.subjectLines
dc.subjectEpothilones
dc.subjectDiscovery
dc.titleSynthesis of methoxylated goniothalamin, aza-goniothalamin and gamma-pyrones and their in vitro evaluation against human cancer cells
dc.typeArtículos de revistas


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