Synthesis, anti-Trypanosoma cruzi activity and quantitative structure relationships of some fluorinated thiosemicarbazones.

Synthesis and spectroscopic characterization of ten fluorinated thiosemicarbazones are reported. All synthesized compounds were evaluated for their anti- Trypanosoma cruzi activity, and the IC 50 values were obtained in the range of 5.64–29.19 μg mL −1 in 24 h of cultures. Among all assayed thiosemicarbazones the 2,3,4-trifluoro-substituted compound showed the higher activity with IC 50 = 5.64 μg mL −1 . QSAR studies involving electronic and hydrophobic parameters, as well as the 13 C NMR chemical shifts of iminic carbon indicated that the deshielding effect caused by the fluorine atoms and their hydrophobicity are significant features for the anti- T. cruzi activity. [ABSTRACT FROM AUTHOR]