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

页码：31 / 36

页数：6

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