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Type: Artigo de periódico
Title: 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.
Author: Bruder, Marjorie
Vendramini-Costa, Débora Barbosa
de Carvalho, João Ernesto
Pilli, Ronaldo Aloise
Abstract: The 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.
Subject: Antineoplastic Agents
Cell Line, Tumor
Cell Survival
Drug Design
Drug Screening Assays, Antitumor
Ht29 Cells
K562 Cells
Mcf-7 Cells
Structure-activity Relationship
Antiproliferative Activity
Cancer Cells
Rights: fechado
Identifier DOI: 10.1016/j.bmc.2013.06.044
Date Issue: 2013
Appears in Collections:Artigos e Materiais de Revistas Científicas - Unicamp

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