dichloro[bis(3,5-dimethyl-1-pyrazolyl)methane-N,N]copper(II) | 95053-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: dichloro[bis(3,5-dimethyl-1-pyrazolyl)methane-N,N]copper(II)
• 英文别名: copper;1-[(3,5-dimethylpyrazol-1-yl)methyl]-3,5-dimethylpyrazole;dichloride
• CAS: 95053-64-8
• 化学式: C₁₁H₁₆Cl₂CuN₄
• 分子量: 338.727
• InChiKey: KAVDIQPCZLKRPU-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -4.18
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[(3,5-二甲基吡唑-1-基)甲基]-3,5-二甲基吡唑 、 copper dichloride 以 丙酮 为溶剂， 反应 0.5h， 以78%的产率得到dichloro[bis(3,5-dimethyl-1-pyrazolyl)methane-N,N]copper(II)
  参考文献：
  名称：

  偶氮配合物与银纳米粒子结合的抗菌活性。

  摘要：

  世卫组织，疾病预防控制中心和食品与药物管理局等卫生组织认为，不断增长的抗菌素耐药性对人类健康安全构成潜在威胁，并以MRSA为例。需要新的抗菌药物和复杂的衍生物来对抗细菌耐药性的发展。合成并分离出六种新的唑衍生物铜和钴配合物，它们为空气稳定的固体，并通过熔点分析，元素分析，热重分析（TGA）以及红外和紫外/可见光谱进行表征。分析和光谱数据表明，该配合物具有1：1（M：L）的化学计量比和四面体的几何值，后者得到DFT计算的支持。金属配合物本身的抗菌活性以及与银纳米颗粒（AgNPs）的结合 通过肉汤微量稀释测定法针对8种具有临床相关性的菌株在体外评估了2μgmL-1）。结果表明，单独的复合物表现出中等的抗菌活性。然而，当金属配合物与AgNPs结合时，它们的抗菌活性增加（在配合物5的情况下达到10倍），同时保持了人类细胞的活力。最小抑菌浓度（MIC50）值在25-500μgmL-1的范围内。因此，

  DOI：

  10.3390/molecules23020361

文献信息

• Copper Binding Agents Acting as Copper Ionophores Lead to Caspase Inhibition and Paraptotic Cell Death in Human Cancer Cells
  作者：Saverio Tardito、Irene Bassanetti、Chiara Bignardi、Lisa Elviri、Matteo Tegoni、Claudio Mucchino、Ovidio Bussolati、Renata Franchi-Gazzola、Luciano Marchiò

  DOI：10.1021/ja109413c

  日期：2011.4.27

  We report a quantitative structure activity relationship study of a new class of pyrazole-pyridine copper complexes that establishes a clear correlation between the ability to promote copper accumulation and cytotoxicity. Intracellular metal accumulation is maximized when ligand lipophilicity allows the complex to rapidly cross the membrane. Copper and ligand follow different uptake kinetics and reach different intracellular equilibrium concentrations. These results support a model in which the ligand acts as an ionophore for the metal ion, cycling between intra- and extracellular compartments as dissociated or complexed entities. When treating cancer cells with structurally unrelated disulfiram and pyrazole-pyridine copper complexes, as well as with inorganic copper, the same morphological and molecular changes were reproduced, indicating that copper overload is responsible for the cytotoxic effects. Copper-based treatments drive sensitive cancer cells toward paraptotic cell death, a process hallmarked by endoplasmic reticulum stress and massive vacuolization in the absence of apoptotic features. A lack of caspase activation, as observed in copper-treated dying cells, is a consequence of metal-mediated inhibition of caspase-3. Thus, copper acts simultaneously as an endoplasmic reticulum (ER) stress inducer and a caspase-3 inhibitor, forcing the cell into caspase-independent paraptotic death. The establishment of a mechanism of action common to different copper binding agents provides a rationale for the exploitation of copper toxicity as an anticancer tool.
• Synthesis of mixed-ligand copper(II) complexes containing bis(pyrazol-1-yl)methane ligands
  作者：Andrei S. Potapov、Andrei I. Khlebnikov

  DOI：10.1016/j.poly.2006.03.016

  日期：2006.10

  Complexes of copper(II) nitrate and chloride with several bis(pyrazol-1-yl)methane derivatives have been prepared and characterized by spectroscopic (IR, UV-Vis) and electrochemical (solution conductivity measurements, cyclic voltammetry) techniques. The complexes react with bidentate (2,2'-bipyridyl and acetylacetone) and monodentate (triphenylphosphine, 1H-benzimidazole, 1H-benzotriazole, 3,5-dimethyl-1H-pyrazole) ligands forming mixed-ligand complexes. (c) 2006 Elsevier Ltd. All rights reserved.