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Type: Artigo de periódico
Title: Synthesis, antiproliferative activity in cancer cells and theoretical studies of novel 6 alpha,7 beta-dihydroxyvouacapan-17 beta-oic acid Mannich base derivatives
Author: Euzebio, FPG
dos Santos, FJL
Pilo-Veloso, D
Alcantara, AFC
Ruiz, ALTG
de Carvalho, JE
Foglio, MA
Ferreira-Alves, DL
de Fatima, A
Abstract: Natural products are great prototypes for the design of new anticancer agents. The plant-derived natural product 6 alpha,7 beta-dihydroxyvouacapan-17 beta-oic acid (1) is promising for the development of more potent antiproliferative agents against human cancer cells. Indeed, its lactone derivative 6 alpha-hydroxyvouacapan-7 beta,17 beta-lactone (2), a non-natural furanoditerpene, exhibited higher anticancer activity than compound 1. Herein, we describe the synthesis and antiproliferative activity of six new Mannich derivatives of compound 2 against nine cancer cell lines. Overall, our results revealed that Mannich derivatives 3-8 were more potent than compound 2 in inhibiting the proliferation of cancer cells. Theoretical studies also supported our findings, revealing the nucleophilic character of furan ring as an important feature for antiproliferative activity of the studied Mannich derivatives. (C) 2010 Elsevier Ltd. All rights reserved.
Subject: 6 alpha,7 beta-Dihydroxyvouacapan-17 beta-oic acid
Mannich base
Furanoditerpene derivatives
Anticancer agents
Natural products
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Citation: Bioorganic & Medicinal Chemistry. Pergamon-elsevier Science Ltd, v. 18, n. 23, n. 8172, n. 8177, 2010.
Rights: fechado
Identifier DOI: 10.1016/j.bmc.2010.10.015
Date Issue: 2010
Appears in Collections:Unicamp - Artigos e Outros Documentos

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