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, Marjorie
dc.creatorVendramini-Costa, Débora Barbosa
dc.creatorde Carvalho, João Ernesto
dc.creatorPilli, Ronaldo Aloise
dc.date2013-Sep
dc.date2015-11-27T13:31:59Z
dc.date2015-11-27T13:31:59Z
dc.date.accessioned2018-03-29T01:18:12Z
dc.date.available2018-03-29T01:18:12Z
dc.identifierBioorganic & Medicinal Chemistry. v. 21, n. 17, p. 5107-17, 2013-Sep.
dc.identifier1464-3391
dc.identifier10.1016/j.bmc.2013.06.044
dc.identifierhttp://www.ncbi.nlm.nih.gov/pubmed/23876338
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/200741
dc.identifier23876338
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1300974
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 α,β-unsaturated ester oxygen atom. These results provide new information on the structure activity relationship of these α,β-unsaturated styryl lactones, thereby further focusing the design of novel candidates.
dc.description21
dc.description5107-17
dc.languageeng
dc.relationBioorganic & Medicinal Chemistry
dc.relationBioorg. Med. Chem.
dc.rightsfechado
dc.rightsCopyright © 2013 Elsevier Ltd. All rights reserved.
dc.sourcePubMed
dc.subjectAntineoplastic Agents
dc.subjectCell Line, Tumor
dc.subjectCell Survival
dc.subjectDrug Design
dc.subjectDrug Screening Assays, Antitumor
dc.subjectFurans
dc.subjectHt29 Cells
dc.subjectHumans
dc.subjectK562 Cells
dc.subjectMcf-7 Cells
dc.subjectPyrones
dc.subjectStructure-activity Relationship
dc.subject2,5-dihydrofuran-2-ones
dc.subjectAntiproliferative Activity
dc.subjectCancer Cells
dc.subjectGoniothalamin
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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