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

被引：11
|
作者：
Santos, Jonas da Silva [1 ]
de Melos, Jorge Luiz R.
Lima, Gerson S. [2 ]
Lyra, Jade Crespo [2 ]
Guedes, Guilherme Pereira [1 ]
Rodrigues-Santos, Claudio Eduardo [1 ]
Echevarria, Aurea [1 ]
机构：
[1] Univ Fed Rural Rio de Janeiro, Dept Quim, BR-23890000 Seropedica, RJ, Brazil
[2] Fiocruz MS, Biomanguinhos, Rio De Janeiro, RJ, Brazil
来源：
JOURNAL OF FLUORINE CHEMISTRY | 2017年 / 195卷
关键词：
Thiosemicarbazones; Antiparasitic activity; QSAR; Trypanosoma cruzi; CHAGAS-DISEASE; SHORT HISTORY; SEMICARBAZONES; BENZNIDAZOLE; STRAINS; C-13; NMR;
D O I：
10.1016/j.jfluchem.2017.01.013
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Synthesis and spectroscopic characterization of ten fluorinated thiosemicarbazones are reported. All synthesized compounds were evaluated for their anti-Trypanosoma cruzi activity, and the IC50 values were obtained in the range of 5.64-29.19 mu gmL(-1) in 24h of cultures. Among all assayed thiosemicarbazones the 2,3,4-trifluoro-substituted compound showed the higher activity with IC50 = 5.64 mu g mL(-1). QSAR studies involving electronic and hydrophobic parameters, as well as the C-13 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. (C) 2017 Elsevier B.V. All rights reserved.
引用
收藏
页码：31 / 36
页数：6
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