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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.)

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

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Author(s):
Barcelos, Rosimeire Coura [1] ; Pastre, Julio Cezar [1] ; Caixeta, Vanessa [1] ; Vendramini-Costa, Debora Barbosa [2, 3] ; de Carvalho, Joao Ernesto [2, 3] ; Pilli, Ronaldo Aloise [1, 2]
Total Authors: 6
Affiliation:
[1] Univ Estadual Campinas, Inst Quim, Dept Quim Organ, BR-13083970 Campinas, SP - Brazil
[2] Univ Estadual Campinas, Inst Biol, Programa Posgrad Biol Celular & Estrutural, 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. 20, n. 11, p. 3635-3651, JUN 1 2012.
Web of Science Citations: 26
Abstract

The 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. (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
FAPESP's process: 10/16990-1 - Synthesis and evaluation of cytotoxic activity of gama-dihydropyrones: goniothalamin and abyssinone II analogues
Grantee:Júlio Cezar Pastre
Support Opportunities: Scholarships in Brazil - Post-Doctoral