In vitro antiparasitic activity of new thiosemicarbazones in strains of Trypanosoma cruzi

Eur J Med Chem. 2014 Nov 24;87:23-9. doi: 10.1016/j.ejmech.2014.09.027. Epub 2014 Sep 9.


In this study thiosemicarbazones derivatives of 5-[(trifluoromethyl)phenylthio]-2-furaldehyde were synthesized and evaluated in terms of their efficiency in challenging the growth of epimastigote forms of Trypanosoma cruzi, the etiological agent of Chagas' disease. A number of compounds were synthesized from 5-bromo-2-furfuraldehyde using nucleophilic aromatic substitution, with a series of trifluoromethyl thiolates, followed by condensation reactions with thiosemicarbazide. Their molecular structures were determined by (1)H, (13)C and (19)F NMR, MS and IR spectroscopy. When tested with T. cruzi, they showed a stronger reaction, similar to nifurtimox and benznidazole, with the 5-[nitro-4-(trifluoromethyl)phenyltio]-2-furaldehyde thiosemicarbazone (compound 4) showing the highest antiparasitic activity. This improved activity may be explained due to the nitro group present in the molecule, which potentiates its activity. The thiosemicarbazone derivatives in this study showed no apoptosis in platelets or monocytes, nor did they induce platelet activation. The trypanocidal activity of these substances represents a good starting point for a medicinal chemistry program aimed at therapy for Chagas' disease.

Keywords: Apoptosis; Platelet activation; Structure–activity relationship; Thiosemicarbazones; Trypanocidal activity.

MeSH terms

  • Apoptosis / drug effects
  • Blood Platelets / drug effects*
  • Blood Platelets / parasitology
  • Cells, Cultured
  • Chagas Disease / drug therapy*
  • Flow Cytometry
  • Humans
  • In Vitro Techniques
  • Molecular Structure
  • Monocytes / drug effects*
  • Monocytes / parasitology
  • Platelet Activation / drug effects*
  • Thiosemicarbazones / chemistry*
  • Trypanocidal Agents / chemistry
  • Trypanocidal Agents / pharmacology*
  • Trypanosoma cruzi / drug effects*


  • Thiosemicarbazones
  • Trypanocidal Agents