Synthesis of compounds with antiproliferative activity as analogues of prenylated natural products existing in Brazilian propolis

  • Pisco L
  • Kordian M
  • Peseke K
 et al. 
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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 μg/ml). © 2006 Elsevier SAS. All rights reserved.

Author-supplied keywords

  • Antiproliferative activity
  • Brazilian propolis
  • Claisen rearrangement
  • Prenylation
  • o-Hydroxy-acetophenone

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Authors

  • Ernesto EstradaUniversity of Strathclyde

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  • Laura Pisco

  • Marcus Kordian

  • Klaus Peseke

  • Holger Feist

  • Dirk Michalik

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