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新型3-吲哚甲醛的1-N-取代硫代氨基脲的钯(II)配合物:表征及对溶组织内阿米巴的抗阿米巴评估

New Pd(II) complexes of the synthesized 1-N-substituted thiosemicarbazones of 3-indole carboxaldehyde: characterization and antiamoebic assessment against E. histolytica.

作者信息

Husain Kakul, Bhat Abdul Roouf, Azam Amir

机构信息

Department of Chemistry, Jamia Millia Islamia, Jamia Nagar, New Delhi 110025, India.

出版信息

Eur J Med Chem. 2008 Sep;43(9):2016-28. doi: 10.1016/j.ejmech.2007.12.002. Epub 2007 Dec 14.

Abstract

Reaction of 3-indole carboxaldehyde with aminothiocarbonyl hydrazines resulted in the formation of 3-indole carboxaldehyde thiosemicarbazones (TSCs) 1-13. The synthesized thiosemicarbazones were used as ligands in the formation of [Pd(TSC)Cl2] complexes with palladium(II) metal ion precursor, [Pd(DMSO)2Cl2]. The chemical structures of all the compounds were established by electronic, IR, 1H NMR and 13C NMR spectral data. The structure of the complexes was further established by FABMS and DTA. It is concluded that the thione sulphur and the azomethine nitrogen atom of the ligands are bonded to the metal ion. The testing of the antiamoebic activity of these compounds against the protozoan parasite Entamoeba histolytica suggests that compounds 5, 3a, 5a and 8a-13a might be endowed with important antiamoebic properties since they showed less IC50 values than metronidazole. Moreover, compound 12a displays remarkable antiamoebic activity than metronidazole (IC50 values of 0.29 vs 1.81 microM, respectively). MTT assay showed that the compounds are non-toxic to human kidney epithelial cell line.

摘要

3-吲哚甲醛与氨基硫代羰基肼反应生成了3-吲哚甲醛缩氨基硫脲(TSCs)1-13。合成的缩氨基硫脲用作配体,与钯(II)金属离子前体[Pd(DMSO)2Cl2]形成[Pd(TSC)Cl2]配合物。所有化合物的化学结构通过电子、红外、1H NMR和13C NMR光谱数据确定。配合物的结构通过FABMS和DTA进一步确定。得出结论,配体的硫酮硫和偶氮甲碱氮原子与金属离子键合。这些化合物对原生动物寄生虫溶组织内阿米巴的抗阿米巴活性测试表明,化合物5、3a、5a和8a-13a可能具有重要的抗阿米巴特性,因为它们的IC50值比甲硝唑低。此外,化合物12a显示出比甲硝唑更显著的抗阿米巴活性(IC50值分别为0.29和1.81 microM)。MTT试验表明这些化合物对人肾上皮细胞系无毒。

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