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Ru(ii)–N-heterocyclic carbene complexes: synthesis, characterization, transfer hydrogenation reactions and biological determination

机译:Ru(ii)–N-杂环卡宾配合物:合成,表征,转移加氢反应和生物学测定

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A series of ruthenium( II ) complexes with N-heterocyclic carbene ligands were successfully synthesized by transmetalation reactions between silver( I ) N-heterocyclic carbene complexes and [RuCl _(2) ( p -cymene)] _(2) in dichloromethane under Ar conditions. All new compounds were characterized by spectroscopic and analytical methods. These ruthenium( II )–NHC complexes were found to be efficient precatalysts for the transfer hydrogenation of ketones by using 2-propanol as the hydrogen source in the presence of KOH as a co-catalyst. The antibacterial activity of ruthenium N-heterocyclic carbene complexes 3a–f was measured by disc diffusion method against Gram positive and Gram-negative bacteria. Compounds 3d exhibited potential antibacterial activity against five bacterial species among the six used as indicator cells. The product 3e inhibits the growth of all the six tested microorganisms. Moreover, the antioxidant activity determination of these complexes 3a–f , using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azinobis-3-ethylbenzothiazoline-6-sulphonic acid (ABTS) as reagent, showed that compounds 3b and 3d possess DPPH and ABTS antiradical activities. From a concentration of 1 mg ml ~(?1) , these two complexes presented a similar scavenging activity to that of the two used controls gallic acid (GA) and butylated hydroxytoluene (BHT). From a concentration of 10 mg ml ~(?1) , the percentage inhibition of complexes 3b and 3d was respectively 70% and 90%. In addition, these two Ru–NHC complexes exhibited antifungal activity against Candida albicans . Investigation of the anti-acetylcholinesterase activity of the studied complexes showed that compounds 3a , 3b , 3d and 3e exhibited good activity at 100 μg ml ~(?1) and product 3d is the most active. In a cytotoxicity study the complexes 3 were evaluated against two human cancer cell lines MDA-MB-231 and MCF-7. Both 3d and 3e complexes were found to be active against the tested cell lines showing comparable activity with examples in the literature.
机译:通过银(I)N-杂环卡宾配合物与[RuCl _(2)(p-Cymene)] _(2)在二氯甲烷中的重金属化反应成功地合成了一系列具有N-杂环卡宾配体的钌(II)配合物Ar条件。所有新化合物都通过光谱和分析方法进行了表征。发现这些钌(II)–NHC络合物是有效的预催化剂,在KOH作为助催化剂的情况下,使用2-丙醇作为氢源,可以转移酮的氢化反应。圆盘扩散法测定了钌N-杂环卡宾配合物3a-f对革兰氏阳性和革兰氏阴性细菌的抗菌活性。化合物3d对用作指示细胞的六种细菌中的五种细菌表现出潜在的抗菌活性。产物3e抑制所有六个测试微生物的生长。此外,使用2,2-二苯基-1-吡啶并肼基(DPPH)和2,2'-叠氮基双-3-乙基苯并噻唑啉-6-磺酸(ABTS)作为试剂测定这些配合物3a-f的抗氧化活性表明,化合物3b和3d具有DPPH和ABTS抗自由基活性。从1mg / ml〜(-1)的浓度,这两种络合物表现出与两种所用的对照没食子酸(GA)和丁基化羟基甲苯(BHT)相似的清除活性。从10mg / ml〜(Δ1)的浓度,配合物3b和3d的抑制百分率分别为70%和90%。此外,这两种Ru–NHC复合物还对白色念珠菌具有抗真菌活性。对所研究的复合物的抗乙酰胆碱酯酶活性的研究表明,化合物3a,3b,3d和3e在100μg/ ml(?1)下表现出良好的活性,而产物3d是最具活性的。在细胞毒性研究中,针对两种人类癌细胞系MDA-MB-231和MCF-7评估了复合物3。发现3d和3e复合物均对被测试的细胞系具有活性,显示出与文献中的实施例相当的活性。

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