Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/79232
Type: Artigo de periódico
Title: Synthesis of compounds with antiproliferative activity as analogues of prenylated natural products existing in Brazilian propolis
Author: Pisco, L
Kordian, M
Peseke, K
Feist, H
Michalik, D
Estrada, E
Carvalho, J
Hamilton, G
Rando, D
Quincoces, J
Abstract: This work describes the syntheses and antitumoral properties of five prenyl compounds from which antiproliferative activities were predicted by using the TOPS-MODE approach, a computational method for drug design. The syntheses of 2-(3-methylbut-2-enyloxy)acetophenone (2), 2-hydroxy-5-(3-methylbut-2-enyl)acetophenone (3), 2-hydroxy-3-(1,1-dimethylallyl)acetophenone (4), and 5-(3-methylbut-2-enyl)-2-(3-methylbut-2-enyloxy)acetophenone (5) were realized by O-prenylation of phenolic compounds with prenyl bromide and by Claisen rearrangement, respectively. Reaction of 2-hydroxy-5-(3-methylbut-2-enyl)acetophenone 3 under Vilsmeier-Haack conditions with phosphoryl chloride and N, N-dimethylformamide yielded 6-(3-methylbut-2-enyl)chromone-3-carbaldehyde (6). The compounds were tested for their cytotoxicity, toward a diverse panel of cultured human tumor cell lines. Compound 3 showed significant selective cytotoxic activity (IC50 < 9 mu g/ml). (c) 2006 Elsevier SAS. All rights reserved.
Subject: o-hydroxy-acetophenone
prenylation
claisen rearrangement
Brazilian propolis
antiproliferative activity
Country: França
Editor: Elsevier France-editions Scientifiques Medicales Elsevier
Rights: fechado
Identifier DOI: 10.1016/j.ejmech.2005.10.020
Date Issue: 2006
Appears in Collections:Unicamp - Artigos e Outros Documentos

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