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首页> 外文期刊>Dalton transactions: An international journal of inorganic chemistry >Copper(II) complexes of functionalized 2,2 ':6 ',2 ''-terpyridines and 2,6-di(thiazol-2-yl)pyridine: structure, spectroscopy, cytotoxicity and catalytic activity
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Copper(II) complexes of functionalized 2,2 ':6 ',2 ''-terpyridines and 2,6-di(thiazol-2-yl)pyridine: structure, spectroscopy, cytotoxicity and catalytic activity

机译：铜（II）官能化2,2'：6'，2'' - 吡啶和2,6-二（噻唑-2-基）吡啶：结构，光谱，细胞毒性和催化活性

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Six new copper(II) complexes with 2,2':6',2''-terpyridine (4'-R-n-terpy) [1 (R-1 = furan-2-yl), 2 (R-2 = thiophen-2-yl), and 3 (R-3 = 1-methyl-1H-pyrrol-2-yl)] and 2,6-di(thiazol-2-yl) pyridine derivatives (R-n-dtpy) [4 (R-1), 5 (R-2), and 6 (R-3)] have been synthesized by a reaction between copper(II) chloride and the corresponding ligand. The complexes have been characterized by UV-vis and IR spectroscopy, and their structures have been determined by X-ray analysis. The antiproliferative potential of copper(II) complexes of 2,2': 6', 2''-terpyridine and 2,6-di(thiazol-2-yl) pyridine derivatives towards human colorectal (HCT116) and ovarian (A2780) carcinoma as well as towards lung (A549) and breast adenocarcinoma (MCF7) cell lines was examined. Complex 1 and complex 6 were found to have the highest antiproliferative effect on A2780 ovarian carcinoma cells, particularly when compared with complex 2, 3 with no antiproliferative effect. The order of cytotoxicity in this cell line is 6 > 1 > 5 > 4 > 2 approximate to 3. Complex 2 seems to be much more specific towards colorectal carcinoma HCT116 and lung adenocarcinoma A549 cells. The viability loss induced by the complexes agrees with Hoechst 33258 staining and typical morphological apoptotic characteristics like chromatin condensation and nuclear fragmentation. The specificity towards different types of cell lines and the low cytotoxic activity towards healthy cells are of particular interest and are a positive feature for further developments. Complexes 1-6 were also tested in the oxidation of alkanes and alcohols with hydrogen peroxide and tert-butyl-hydroperoxide (TBHP). The most active catalyst 4 gave, after 120 min, 0.105 M of cyclohexanol + cyclohexanone after reduction with PPh3. This concentration corresponds to a yield of 23% and TON = 210. Oxidation of cis-1,2-dimethylcyclohexane with m-CPBA catalyzed by 4 in the presence of HNO3 gave a product of a stereoselective reaction (trans/cis = 0.47). Oxidation of secondary alcohols afforded the target ketones in yields up to 98% and TON = 630.
机译：六个新的铜（II）配合物，2,2'：6'，2'' - 吡啶（4'-RN-TERPY）[1（R-1 = Furan-2-Y1），2（R-2 =噻吩-2-y1）和3（R-3 = 1-甲基-1H-吡咯-2-基）]和2,6-二（噻唑-2-基）吡啶衍生物（RN-DTPY）[4（r通过铜（II）氯化物和相应配体之间的反应合成了-1），5（R-2）和6（R-3）。复合物的特征在于UV-Vis和IR光谱，并且它们的结构已经通过X射线分析确定。 2,2'：6'，2' - 三吡啶和2,6-二（噻唑-2-基）吡啶衍生物朝向人结肠直肠（HCT116）和卵巢癌（A2780）癌的抗增殖潜力除了检查肺（A549）和乳腺腺癌（MCF7）细胞系。发现复合物1和复合物6对A2780卵巢癌细胞具有最高的抗增殖作用，特别是与复合物2,3相比，没有抗增殖作用。该细胞系中细胞毒性的顺序为6> 1> 5> 4 2近似为3.复合物2似乎更具体地朝大肠病癌HCT116和肺腺癌A549细胞。复合物诱导的活力损失同意Hoechst 33258染色和典型的形态凋亡特征，如染色质缩合和核碎片。对不同类型的细胞系和朝向健康细胞的低细胞毒性活性的特异性特别感兴趣，并且是进一步发展的阳性特征。还在用过氧化氢和叔丁基 - 氢过氧化物（TBHP）的烷烃和醇的氧化物和醇中进行复合物1-6。在120分钟后，最活性的催化剂4得到0.105μm的环己醇+环己酮在用PPH3进行还原后。该浓度对应于23％和TON = 210的产率。在HNO 3存在下催化4℃-1,2-二甲基环己烷的氧化在HNO 3存在下，得到了立体选择反应的产物（反式/顺式= 0.47）。仲醇的氧化得到的靶酮，产率高达98％和吨= 630。

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