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5-硝基噻吩-2-甲醛缩氨基硫脲及其钯(II)和钌(II)配合物的合成、表征及体外抗阿米巴活性

synthesis, characterization and in vitro antiamoebic activity of 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones and their Palladium (II) and Ruthenium (II) complexes.

作者信息

Singh Shailendra, Bharti Neelam, Naqvi Fehmida, 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. 2004 May;39(5):459-65. doi: 10.1016/j.ejmech.2004.02.003.

Abstract

Synthesis of new Palladium(II) and Ruthenium(II) complexes of the type, [Pd(L)Cl(2)] and [Ru(eta(4)-C(8)H(12))(L)Cl(2)] [where, L = thiosemicarbazones derived from 5-nitrothiophene-2-carboxaldehyde and cycloalkylaminothiocarbonyl hydrazines] have been isolated by the reaction of [Pd(DMSO)(2)Cl(2)] and [Ru(eta(4)-C(8)H(12))(CH(3)CN)(2)Cl(2)] with 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones. The spectral data revealed that the thiosemicarbazones act as bidentate ligands, making use of thionic sulphur and the azomethine nitrogen atom for coordination to the central metal ion. Microdilution method was used for the assessment of antiamoebic activity of all the compounds against HK-9 strain of Entamoeba histolytica. Among all the thiosemicarbazones, 5-NT-4-BPTSCN (3) showed significant antiamoebic activity (IC(50) - 2.56 microM). Enhancement of antiamoebic activity resulted by introducing palladium and ruthenium metals in the thiosemicarbazone moiety. All the Pd(II) and Ru(II) complexes of 5-nitrothiophene-2-carboxaldehyde thiosemicarbazones were found more active then their respective ligands. The complexes 1a-4a, 1b and 3b showed antiamoebic activity.

摘要

通过[Pd(DMSO)₂Cl₂]和[Ru(η⁴-C₈H₁₂)(CH₃CN)₂Cl₂]与5-硝基噻吩-2-甲醛硫代卡巴腙反应,分离得到了新型的[Pd(L)Cl₂]和[Ru(η⁴-C₈H₁₂)(L)Cl₂]类型的钯(II)和钌(II)配合物[其中,L = 由5-硝基噻吩-2-甲醛和环烷基氨基硫代羰基肼衍生的硫代卡巴腙]。光谱数据表明,硫代卡巴腙作为双齿配体,利用硫代硫和甲亚胺氮原子与中心金属离子配位。采用微量稀释法评估所有化合物对溶组织内阿米巴HK-9菌株的抗阿米巴活性。在所有硫代卡巴腙中,5-NT-4-BPTSCN(3)表现出显著的抗阿米巴活性(IC₅₀ - 2.56 μM)。在硫代卡巴腙部分引入钯和钌金属可增强抗阿米巴活性。发现所有5-硝基噻吩-2-甲醛硫代卡巴腙的钯(II)和钌(II)配合物比其各自的配体更具活性。配合物1a - 4a、1b和3b表现出抗阿米巴活性。

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