The present work describes the synthesis, structural characterization and trypanocidal activity studies of twelve compounds, eight thiosemicarbazones (TSCs) and four dithiocarbazates (DTCs) containing pyrazoline ring in their structures, as well as in the study of complex formation of a DTC with Ga^III. The TSCs and DTCs were obtained from condensation reactions involving a & beta;-diketone and a dithiocarbazate or thiosemicarbazide, respectively. From 1-phenyl-1,3-butanedione (benzoylacetone) and 4-R-thiosemicarbazide were obtained TSCs the name 5-hydroxy-3-methyl-5-phenyl-pyrazoline-1-(4-R-thiosemicarbazone), identified as H₂bt, H₂bmt, H₂bet and H₂bpt, R = H, Me, Et, Ph, respectively. Changing the & beta;-diketone for 4,4,4-trifluoro-1-phenyl-1,3-butanedione result in TSCs the name 5-hydroxy-3-phenyl-5-trifluoromethyl-pyrazoline-1-(4-R-thiosemicarbazone), identified as H₂ft, H₂fmt, H₂fet and H₂fpt, R = H, Me, Et, Ph, respectively. Similarly, the DTCs with name 5-hydroxy-3-methyl-5-phenyl-pyrazoline-1-(S-p-R-benzyldithiocarbazate), H₂bdtc and H₂mbdtc to R = H and OMe, respectively, were obtained from benzoylacetone and S-p-R-benzyldithiocarbazate, while DTCs 5-hydroxy-3-phenyl-5-trifluoromethyl-pyrazoline-1-(S-p-R-benzyldithiocarbazate), H₂fdtc and H₂mfdtc to R = H and OMe, respectively, are formed with 4,4,4-trifluoro-1-phenyl-1,3-butanedione. The compounds were characterized by various techniques such as elemental analysis, infrared spectroscopy (IR), mass spectrometry, nuclear magnetic resonance of hydrogen and fluorine (¹H and ¹⁹F NMR) and single crystals X-ray diffraction. The TSCs and DTCs were evaluated for their anti-T. cruzi activity and cytotoxicity against macrophage cells, making it possible to evaluate the effects of substituent peripheral groups. In these studies, other two new compounds than H₂bdtc whose activity is known, were considered promising, H₂bt and H₂bmt, having superior activity, CC_50try values 9.91 and 6.85 µM, respectively, compared with benznidazole used as reference (CC_50try = 10.6 µM). The compounds also show selective with CC₅₀> 100 µM for J774 macrophage cells. In the complexation studies with Ga^III using H₂bdtc it is possible to obtain two new complex, varying the reaction conditions, being a mononuclear, [Ga(bdtc)(Hbdtc)]·CH₃OH, and other dinuclear [Ga₂(bdtc)₂(µ OCH₃)₂]^.CH₂Cl₂, which were characterized both in solution and in solid state, having their structures determined by single crystals X-ray diffraction. Both having Ga^III pentacoordenate, with distortion of coordination geometry between trigonal bipyramidal and square pyramidal. When the ligand bdtc^2- coordinated dianionic the form is O,N,S-tridentate, unlike the form S,N-bidentate was observed for the DTC when coordinated monoanionic as bdtc^1-.

The present work describes the synthesis, structural characterization and trypanocidal activity studies of twelve compounds, eight thiosemicarbazones (TSCs) and four dithiocarbazates (DTCs) containing pyrazoline ring in their structures, as well as in the study of complex formation of a DTC with Ga^III. The TSCs and DTCs were obtained from condensation reactions involving a ?-diketone and a dithiocarbazate or thiosemicarbazide, respectively. From 1-phenyl-1,3-butanedione (benzoylacetone) and 4-R-thiosemicarbazide were obtained TSCs the name 5-hydroxy-3-methyl-5-phenyl-pyrazoline-1-(4-R-thiosemicarbazone), identified as H₂bt, H₂bmt, H₂bet and H₂bpt, R = H, Me, Et, Ph, respectively. Changing the ?-diketone for 4,4,4-trifluoro-1-phenyl-1,3-butanedione result in TSCs the name 5-hydroxy-3-phenyl-5-trifluoromethyl-pyrazoline-1-(4-R-thiosemicarbazone), identified as H₂ft, H₂fmt, H₂fet and H₂fpt, R = H, Me, Et, Ph, respectively. Similarly, the DTCs with name 5-hydroxy-3-methyl-5-phenyl-pyrazoline-1-(S-p-R-benzyldithiocarbazate), H₂bdtc and H₂mbdtc to R = H and OMe, respectively, were obtained from benzoylacetone and S-p-R-benzyldithiocarbazate, while DTCs 5-hydroxy-3-phenyl-5-trifluoromethyl-pyrazoline-1-(S-p-R-benzyldithiocarbazate), H₂fdtc and H₂mfdtc to R = H and OMe, respectively, are formed with 4,4,4-trifluoro-1-phenyl-1,3-butanedione. The compounds were characterized by various techniques such as elemental analysis, infrared spectroscopy (IR), mass spectrometry, nuclear magnetic resonance of hydrogen and fluorine (¹H and ¹⁹F NMR) and single crystals X-ray diffraction. The TSCs and DTCs were evaluated for their anti-T. cruzi activity and cytotoxicity against macrophage cells, making it possible to evaluate the effects of substituent peripheral groups. In these studies, other two new compounds than H₂bdtc whose activity is known, were considered promising, H₂bt and H₂bmt, having superior activity, CC_50try values 9.91 and 6.85 µM, respectively, compared with benznidazole used as reference (CC_50try = 10.6 µM). The compounds also show selective with CC₅₀> 100 µM for J774 macrophage cells. In the complexation studies with Ga^III using H₂bdtc it is possible to obtain two new complex, varying the reaction conditions, being a mononuclear, [Ga(bdtc)(Hbdtc)]·CH₃OH, and other dinuclear [Ga₂(bdtc)₂(?-OCH₃)₂]·CH₂Cl₂, which were characterized both in solution and in solid state, having their structures determined by single crystals X-ray diffraction. Both having Ga^III pentacoordenate, with distortion of coordination geometry between trigonal bipyramidal and square pyramidal. When the ligand bdtc^2- coordinated dianionic the form is O,N,S-tridentate, unlike the form S,N-bidentate was observed for the DTC when coordinated monoanionic as bdtc^1-.