Design, synthesis and in vitro evaluation against human cancer cells of 5-methyl-5-styryl-2,5-dihydrofuran-2-ones, a new series of goniothalamin analogues

dc.creatorBruder, M
dc.creatorVendramini-Costa, DB
dc.creatorde Carvalho, JE
dc.creatorPilli, RA
dc.date2013
dc.dateSEP 1
dc.date2014-07-30T14:38:50Z
dc.date2015-11-26T17:29:30Z
dc.date2014-07-30T14:38:50Z
dc.date2015-11-26T17:29:30Z
dc.date.accessioned2018-03-29T00:16:30Z
dc.date.available2018-03-29T00:16:30Z
dc.identifierBioorganic & Medicinal Chemistry. Pergamon-elsevier Science Ltd, v. 21, n. 17, n. 5107, n. 5117, 2013.
dc.identifier0968-0896
dc.identifier1464-3391
dc.identifierWOS:000323294600026
dc.identifier10.1016/j.bmc.2013.06.044
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/61257
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/61257
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1285295
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionThe present work describes the preparation of a novel series of compounds based on the structure of goniothalamin (1), a natural styryl lactone with known cytotoxic and antiproliferative activities against a variety of cancer cell lines. A focused library of 17 goniothalamin analogues displaying the 5-methyl-2,5-dihydrofuran-2-one motif were prepared, and their cytotoxicity evaluated. While the analogues bearing methoxy and/or hydroxy groups on the aromatic moiety usually were at least three times less potent than the lead compound (1), ortho and para-trifluoromethyl analogues 10 and 11 exhibited levels of cytotoxicity similar to goniothalamin (1) against most cancer cell lines evaluated. One could suggest that the electronic effect of the trifluoromethyl group activates the inhibitor's electrophilic site via reduction of the electron density of the alpha,beta-unsaturated ester oxygen atom. These results provide new information on the structure activity relationship of these alpha,beta-unsaturated styryl lactones, thereby further focusing the design of novel candidates. (C) 2013 Elsevier Ltd. All rights reserved.
dc.description21
dc.description17
dc.description5107
dc.description5117
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
dc.descriptionFAPESP [2010/06178-8, 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.subject2,5-Dihydrofuran-2-ones
dc.subjectTrans 3,4,5,4'-tetramethoxystilbene Dmu-212
dc.subjectChemopreventive Agent Resveratrol
dc.subjectStyryl-lactone Goniothalamin
dc.subjectAnticancer Drug Screen
dc.subjectCytotoxic Activity
dc.subjectAsymmetric-synthesis
dc.subjectNatural-products
dc.subjectTumor
dc.subjectEnantiomers
dc.subjectApoptosis
dc.titleDesign, synthesis and in vitro evaluation against human cancer cells of 5-methyl-5-styryl-2,5-dihydrofuran-2-ones, a new series of goniothalamin analogues
dc.typeArtículos de revistas


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