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New trypanocidal hybrid compounds from the association of hydrazone moieties and benzofuroxan heterocycle

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2008-07
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Porcal, Williams
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New trypanocidal hybrid compounds from the association of hydrazone moieties and benzofuroxan heterocycle
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Author
  • Porcal, Williams;
  • Hernández, Paola;
  • Boiani, Lucía;
  • Boiani, Mariana;
  • Ferreira, Ana;
  • Chidichimo, Agustina;
  • Cazzulo, Juan J.;
  • Olea Azar, Claudio;
  • González, Mercedes;
  • Cerecetto, Hugo;
Abstract
Hybrid compounds containing hydrazones and benzofuroxan pharmacophores were designed as potential Trypanosoma cruzi-enzyme inhibitors. The majority of the designed compounds was successfully synthesized and biologically evaluated displaying remarkable in vitro activity against different strains of T. cruzi. Unspecific cytotoxicity was evaluated using mouse macrophages, displaying isothiosemicarbazone 10 and thiosemicarbazone 12 selectivity indexes (macrophage/parasite) of 21 and 27, respectively. In addition, the mode of anti-trypanosomal action of the derivatives was investigated. Some of these derivatives were moderate inhibitors of cysteinyl active site enzymes of T. cruzi, cruzipain and trypanothione reductase. ESR experiments using T. cruzi microsomal fraction suggest that the main mechanism of action of the trypanocidal effects is the production of oxidative stress into the parasite.
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URI: https://repositorio.uchile.cl/handle/2250/120851
ISSN: 0968-0896
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Bioorganic & Medicinal Chemistry, Volume 16, Issue 14, 15, Pages 6995-7004, 2008
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