Structure–activity relationship study of thiosemicarbazones on an African trypanosome: Trypanosoma brucei brucei

Fatondji, Houssou Raymond;Kpoviessi, Dossou Sika Salomé;Gbaguidi, Fernand;Bero, Joanne;Accrombessi, Georges Coffi;et.al.
(2013) Medicinal Chemistry Research : an international journal for rapid communications on design and mechanisms of action of biologically active agents — Vol. 22, n° 5, p. 2151-2162 (2013)

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Authors
  • Fatondji, Houssou Raymond
    Author
  • Kpoviessi, Dossou Sika Salomé
    Author
  • Gbaguidi, Fernand
    Author
  • Bero, JoanneUCLouvain
    Author
  • Hannaert, VéroniqueUCLouvain
    Author
  • Quetin-Leclercq, JoëlleUCLouvain
    Author
  • Poupaert, JacquesUCLouvain
    Author
  • Accrombessi, Georges Coffi
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Abstract
To explore the structure–activity relationships of thiosemicarbazones on African trypanosome: Trypanosoma brucei brucei, a series of thirty-five thiosemicarbazones (1–35) have been synthesized and characterized by their 1H NMR, 13C NMR, and FT-IR spectra. All compounds were tested for trypanocidal activity using the method ‘‘Lilit alamar blue’’. The comparison of trypanocidal power of thiosemicarbazones was performed considering their structures. This study that was done using acetophenone thiosemicarbazone (1) as basic model, showed that: (a) the presence of lipophilic substituents in para position on benzene ring, (b) substitution of benzene ring and (c) substitution of hydrogen of thioamide function by a phenyl, strongly influence trypanocidal activity. The various modifications to basic structure (1) allowed the synthesis of 1-(4-chlorophenyl) ethylidene-4-phenyl-thiosemicarbazide (34). With a trypanocidal activity of 3.97 lM, this compound is the most active of the series
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Fatondji, H. R., Kpoviessi, D. S. S., Gbaguidi, F., Bero, J., Hannaert, V., Quetin-Leclercq, J., Poupaert, J., Moudachirou, M., & Accrombessi, G. C. (2013). Structure–activity relationship study of thiosemicarbazones on an African trypanosome: Trypanosoma brucei brucei. Medicinal Chemistry Research : an international journal for rapid communications on design and mechanisms of action of biologically active agents, 22(5), 2151-2162. https://doi.org/10.1007/s00044-012-0208-6 (Original work published 2013)