The synthesis and antiparasitic activity of aryl- and ferrocenyl-derived thiosemicarbazone ruthenium(II)-arene complexes
The synthesis and antiparasitic activity of aryl- and ferrocenyl-derived thiosemicarbazone ruthenium(II)-arene complexes
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DOI：
10.1039/c3dt32740j
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发表时间：
2013-01-01
影响因子：
4
通讯作者：
Smith, Gregory S.
中科院分区：
文献类型：
--
作者：
Adams, Muneebah;Li, Yiqun;Smith, Gregory S.
通过一般的席夫碱缩合反应，以中等产率合成了一系列芳基官能化和二茂铁基缩氨基硫脲化合物(L1-L4)。缩氨基硫脲(TSC)配体与Ru(Ar)(Mu-Cl)Cl](2)(Ar=苯；对伞花烃)反应，合成了一系列阳离子单核Ru(II)-芳烃缩氨基硫脲配合物[Ru(Cl)(TSC)(Ar)]Cl(1-8)。缩氨基硫脲配体作为双齿螯合配体，通过亚胺氮和硫酮硫原子与Ru(II)离子配位。用核磁共振、红外光谱和ESI+-MS对缩氨基硫脲配体及其金属络合物进行了表征。用单晶X-射线衍射法测定了单核Ru(II)-芳烃缩氨基硫脲配合物(6)的分子结构。进一步评价了Ru(II)-芳烃缩氨基硫脲配合物对恶性疟原虫氯喹敏感株(NF54)和氯喹抗性株(DD2)以及阴道毛滴虫G3株的体外抗寄生活性。
A series of aryl-functionalized and ferrocenyl monothiosemicarbazone compounds (L1-L4) were synthesized in moderate yields via a general Schiff-base condensation reaction. The thiosemicarbazone (TSC) ligands were reacted with the ruthenium dimer [Ru(Ar)(mu-Cl)Cl](2) (Ar = benzene; p-cymene) to yield a series of cationic mononuclear ruthenium(II)-arene thiosemicarbazone complexes of the general type [Ru(Cl)(TSC)(Ar)]Cl (1-8). The thiosemicarbazone ligands act as bidentate chelating ligands that coordinate to the ruthenium(II) ion via the imine nitrogen and the thione sulfur atoms. The thiosemicarbazone ligands, as well as their metal complexes, were characterized by NMR, IR spectroscopy and ESI+-mass spectrometry. The molecular structure of the mononuclear ruthenium(II)-arene thiosemicarbazone complex (6) was determined by single-crystal X-ray diffraction analysis. The ruthenium(II)-arene thiosemicarbazone complexes were further evaluated for their in vitro antiparasitic activities against the Plasmodium falciparum chloroquine-sensitive (NF54) and chloroquine-resistant (Dd2) strains, as well as the G3 strain of Trichomonas vaginalis.