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|Type:||Artigo de periódico|
|Title:||Synthesis of compounds with antiproliferative activity as analogues of prenylated natural products existing in Brazilian propolis|
|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.|
|Editor:||Elsevier France-editions Scientifiques Medicales Elsevier|
|Appears in Collections:||Unicamp - Artigos e Outros Documentos|
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