2-(2-(((1'-methyl-2'-imidazolyl)methylene)amino)ethyl)pyridine | 173412-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(2-(((1'-methyl-2'-imidazolyl)methylene)amino)ethyl)pyridine
• 英文别名: 1-(1-methylimidazol-2-yl)-N-(2-pyridin-2-ylethyl)methanimine
• CAS: 173412-72-1
• 化学式: C₁₂H₁₄N₄
• 分子量: 214.27
• InChiKey: BTYWYNAHHRHOJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-(((1'-methyl-2'-imidazolyl)methylene)amino)ethyl)pyridine 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以70%的产率得到(1-methyl-1H-imidazol-2-ylmethyl)(pyrid-2-ylethyl)amine
  参考文献：
  名称：

  使用铜（II）配合物基于荧光的水和甲醇介质中一氧化氮的检测。

  摘要：

  发现在脱气的甲醇或水溶液（缓冲于pH 7.2）中，荧光配体的铜（II）配合物1的猝灭荧光强度在暴露于一氧化氮时会重新出现。因此，它可以用作基于荧光的一氧化氮传感器。已经发现本发明的配合物可用于检测甲醇和pH 7.2缓冲水介质中的纳摩尔量的一氧化氮。

  DOI：

  10.1039/c0cc04054a
• 作为产物：
  描述：

  2-(2-氨乙基)吡啶 、 1-甲基-1H-咪唑-2-甲醛 以 甲醇 为溶剂， 以100%的产率得到2-(2-(((1'-methyl-2'-imidazolyl)methylene)amino)ethyl)pyridine
  参考文献：
  名称：

  铜配合物作为溶胞多糖单加氧酶的生物启发模型。

  摘要：

  我们在这里报告两个铜配合物，作为溶解性多糖单加氧酶（参与顽固性多糖分解的单核含铜酶）的第一个功能模型。这些复合物具有类似于酶的结构和光谱性质。另外，它们催化模型底物对-硝基苯基-β- d-吡喃葡萄糖苷的氧化裂解。更重要的是，在反应条件下检测到特别稳定的氢过氧化铜（II）中间体。

  DOI：

  10.1021/acs.inorgchem.6b02165

文献信息

• Insertion Reactions Involving Palladium Complexes with Nitrogen Ligands. 2. Carbon monoxide and Alkene Insertion Reactions with Novel Palladium Compounds Containing Terdentate Ligands
  作者：Richard E. Rülke、Vincent E. Kaasjager、Dave Kliphuis、Cornelis J. Elsevier、Piet W. N. M. van Leeuwen、Kees Vrieze、Kees Goubitz

  DOI：10.1021/om9504361

  日期：1996.1.23

  containing trinitrogen ligands (N-N-N)Pd(Me)(Y) (N-N-N = trinitrogen ligand; Y = Cl-, CF3SO3-, 4-Me-C6H4SO3-) have been synthesized and characterized by spectroscopic methods. The coordination mode of the trinitrogen ligand depends not only on the rigidity of the ligand but also on the solvent and on the anion Y. With the weakly coordinating ligands CF3SO3- and BF4- the trinitrogen ligands readily adopt a

  含有trinitrogen配体（NNN）的Pd（ME）（Y）中性和离子methylpalladium化合物（NNN = trinitrogen配位体; Y =氯-，CF 3 SO 3 -，4-ME-C 6 H ^ 4 SO 3 - ）已被合成并通过分光镜方法表征。所述trinitrogen的协调式配体不仅取决于配体的刚性，而且对溶剂和在阴离子Y.随着弱配位的配体CF 3 SO 3 -和BF 4 -的配位体trinitrogen容易地采用一个terdentate协调模式，导致型[络合物（σ 3-NNN）Pd（Me）] Y。在methylchloropalladium化合物，柔性trinitrogen配体采用的二齿配位方式，导致复合物（σ 2 -NNN）的Pd（ME）（CL），而terdentate协调模式已经发现刚性配体，导致所述离子配合物[ （σ 3 -NNN）的Pd（]我氯。极性溶剂，如
• Fluorescence-based detection of nitric oxide in aqueous and methanol media using a copper(ii) complex
  作者：Biplab Mondal、Pankaj Kumar、Pokhraj Ghosh、Apurba Kalita

  DOI：10.1039/c0cc04054a

  日期：——

  The quenched fluorescent intensity of a copper(II) complex, 1, of a fluorescent ligand, in degassed methanol or aqueous (buffered at pH 7.2) solution, was found to reappear on exposure to nitric oxide. Thus, it can function as a fluorescence based nitric oxide sensor. It has been found that the present complex can be used to sense nanomolar quantities of nitric oxide in both methanol and pH 7.2 buffered-water

  发现在脱气的甲醇或水溶液（缓冲于pH 7.2）中，荧光配体的铜（II）配合物1的猝灭荧光强度在暴露于一氧化氮时会重新出现。因此，它可以用作基于荧光的一氧化氮传感器。已经发现本发明的配合物可用于检测甲醇和pH 7.2缓冲水介质中的纳摩尔量的一氧化氮。
• Reduction of copper(ii) complexes of tridentate ligands by nitric oxide and fluorescent detection of NO in methanol and water media
  作者：Pankaj Kumar、Apurba Kalita、Biplab Mondal

  DOI：10.1039/c1dt10773a

  日期：——

  to paramagnetic quenching, does not display any fluorescence; however, on addition of nitric oxide to a methanol or water solution of complex 4, the fluorescence intensity of the fluorophore has been found to be restored. This is attributed to the reduction of the Cu(II) center by nitric oxide to diamagnetic Cu(I). The turn-on of quenched fluorescence intensity has been observed both in methanol and

  具有三齿N供体配体L 1和L 2的两个铜络合物1和2 [ L 1 =（1-甲基-1 H-咪唑-2-基甲基）-（2-吡啶-2-基乙基）胺，L 2 =（2-吡啶-2-基-乙基）-吡啶-2基-甲胺分别被合成和表征。暴露于一氧化氮后，发现配合物1和2中的铜（II）中心在各种溶剂中均会还原。在乙腈溶剂的还原伴随着在配体骨架上仲胺中心的同时N-亚硝化。分别用配体L 3和L 4制备配合物3和4。L 3和L 4 [ L 3＝ 5-二甲基氨基萘-1-磺酸（1-甲基-1 H-咪唑-2-基甲基）-（2-吡啶-2-基乙基）-酰胺；L 4＝ 5-二甲基氨基萘-1-磺酸（2-吡啶-2-基-乙基）-吡啶-2-基甲基-酰胺]是L 1和L 2的丹磺酰基衍生物。， 分别。由于顺磁性淬灭，配合物4不显示任何荧光。然而，发现将一氧化氮加入到配合物4的甲醇或水溶液中时，荧光团的荧光强度得以恢复。这归因于一氧化氮将Cu（II）中心还
• DNA binding, nuclease activity and cytotoxicity studies of Cu(ii) complexes of tridentate ligands
  作者：Pankaj Kumar、Sukhamoy Gorai、Manas Kumar Santra、Biplab Mondal、Debasis Manna

  DOI：10.1039/c2dt30232b

  日期：——

  Cu(II) complexes of three tridentate ligands, L1, L2 and L3,[ L1, N-((1H-imidazole-2-yl)methyl)-2-(pyridine-2-yl)ethanamine; L2, N-((1-methyl-1H-imidazole-2-yl)methyl)-2-(pyridine-2-yl)ethanamine; L3, 2-(pyridine-2-yl)-N-((pyridine-2-yl)methyl)ethanamine] respectively, were synthesized and characterized. The single crystal X-ray structure of complex 1 reveals the pseudo octahedral coordination geometry around the copper center. Absorption and fluorescence experimental evidence show good DNA binding propensity (in the order of 105 M−1) of the complexes. Thermal denaturation and circular dichroism (CD) analyses reveal minor structural changes of calf thymus (CT) DNA in presence of complexes and groove and/or surface binding of the complexes to CT-DNA. Kinetic DNA cleavage assay shows pseudo-first-order kinetic reaction between the complex and supercoiled (SC) DNA. In addition, mechanistic SC DNA cleavage results show higher DNA cleavage activity in presence of reducing agent, due to the presence of hydroxyl radicals. In vitro cytotoxicity assay of the complexes demonstrate that the complexes have low toxicity for different cancer cell lines and IC50 values were between 37 and 156 μM.

  L1，N-((1-甲基-1H-咪唑-2-基)甲基)-2-(吡啶-2-基)乙胺；L2，N-((1-甲基-1H-咪唑-2-基)甲基)-2-(吡啶-2-基)乙胺；L3，2-(吡啶-2-基)-N-((吡啶-2-基)甲基)乙胺]。络合物 1 的单晶 X 射线结构显示出围绕铜中心的假八面体配位几何。吸收和荧光实验证据表明，复合物具有良好的 DNA 结合倾向（约为 105 M-1）。热变性和圆二色性（CD）分析表明，小牛胸腺（CT）DNA 在复合物的存在下发生了微小的结构变化，复合物与 CT-DNA 的沟槽和/或表面结合。动力学 DNA 裂解测定显示，复合物与超卷曲（SC）DNA 之间发生了伪一阶动力学反应。此外，SC DNA 的机理裂解结果表明，在存在还原剂的情况下，由于羟基自由基的存在，DNA 的裂解活性更高。复合物的体外细胞毒性实验表明，复合物对不同的癌细胞株毒性较低，IC50 值介于 37 和 156 μM 之间。
• Effect of H-bonding on the ambivalence of SCN− towards copper(II)
  作者：Michael G.B. Drew、Debashree Das、Senjuti De、Dipankar Datta

  DOI：10.1016/j.ica.2008.07.007

  日期：2009.4

  Condensations of 2-(2-aminoethyl)pyridine with 4-methylimidazole-5-carboxaldehyde and 1-methyl-2-imidazolecarboxaldehyde generate the tridentate N donor ligands L and L' respectively. Reactions of Cu(NCS)(2) with L and L' yield respectively CuL(SCN)(NCS) (1) containing a CuN4S core and CuL'(NCS)(2) (2) having a CuN5 core. Both the cores are square pyramidal with SCN bound in 1 at the axial position through the S end. This differential behaviour of SCN in the two complexes despite the ligands being very similar, is investigated by DFT calculations at the B3LYP/TZV level. It is found that DFT calculations predict isolation of the Cu(ligand)(NCS)(2) species for both the ligands L and L'. Presence of an offsetting intermolecular H-bonding between the N atom of the thiocyanate and the N-H proton of the ligand L of an adjacent molecule makes the binding of SCN via the S end feasible in 1 resulting in the H-bonded-dimer Cu2L2(SCN)(2)(NCS)(2). The strength of the H-bond is estimated as 27.1 kJ mol (1) from the DFT calculations. The question of such H-bonding does not arise with L' as it lacks in a similar H atom. Dimeric 1 represents a case of two non-interacting spins. (C) 2008 Elsevier B. V. All rights reserved.