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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

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

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Author(s):
Bruder, Marjorie [1] ; Vendramini-Costa, Debora Barbosa [1, 2, 3] ; de Carvalho, Joao Ernesto [2, 3] ; Pilli, Ronaldo Aloise [1]
Total Authors: 4
Affiliation:
[1] Univ Estadual Campinas, Inst Quim, Dept Quim Organ, BR-13083970 Campinas, SP - Brazil
[2] Univ Estadual Campinas, Inst Biol, BR-13083970 Campinas, SP - Brazil
[3] Univ Estadual Campinas, Div Farmacol & Toxicol, Ctr Pluridisciplinar Pesquisas Quim Biol & Agr CP, BR-13083970 Campinas, SP - Brazil
Total Affiliations: 3
Document type: Journal article
Source: Bioorganic & Medicinal Chemistry; v. 21, n. 17, p. 5107-5117, SEP 1 2013.
Web of Science Citations: 16
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 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. (AU)

FAPESP's process: 09/51602-5 - Chemical biology: new natural and synthetic molecular targets against cancer, structural studies, biological evaluation and mode of action
Grantee:Ronaldo Aloise Pilli
Support Opportunities: Research Projects - Thematic Grants