2-((1H-benzimidazol-2-yl)ethyl)pyridin-2-ylmethyleneamine | 1093684-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-((1H-benzimidazol-2-yl)ethyl)pyridin-2-ylmethyleneamine
• 英文别名: 2-(1H-benzimidazol-2-yl)-N-(pyridin-2-ylmethylene)ethanamine；N-[2-(1H-benzimidazol-2-yl)ethyl]-1-pyridin-2-ylmethanimine
• CAS: 1093684-65-1
• 化学式: C₁₅H₁₄N₄
• 分子量: 250.303
• InChiKey: KXMPSUDTNAKMDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  53.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  aqueous cadmium chloride 、 2-((1H-benzimidazol-2-yl)ethyl)pyridin-2-ylmethyleneamine 以 甲醇 为溶剂， 反应 2.0h， 以61%的产率得到
  参考文献：
  名称：

  镉 (II) 与苯并咪唑的卤化物/伪卤化物配合物：合成、晶体结构和荧光特性

  摘要：

  摘要 两种新的双核 Cd(II) 配合物 [CdL1Cl2]2·H2O (1) 和 [CdL1(N3)2]2·CH3OH (2) 和一种双氰胺桥连一维多核网络 [CdL1(μ1,5-dca) )dca]n (3) 的潜在三齿 NNN 供体希夫碱 2-((1H-苯并咪唑-2-基-乙基亚氨基)-甲基)-吡啶 (L1) 和另一个双核 Cd(II) 复合物 [CdL2Cl(dca) ]2 (4) 类似的 NNN 供体席夫碱配体 2-((1H-苯并咪唑-2-基-丙基亚氨基)-甲基)-吡啶 (L2)，已合成并通过元素分析、IR 和单晶 X 表征-射线晶体学。配体L1和L2分别是吡啶-2-甲醛与2-氨基乙基-1H-苯并咪唑和2-氨基丙基-1H-苯并咪唑的[1+1]缩合产物。在配合物 1 和 4 中，两个 Cd(II) 中心由桥连的氯配体结合在一起，而在 2 中，两个 Cd(II) 中心由 μ1,1-叠氮化物离子桥接。配合物

  DOI：

  10.1016/j.molstruc.2017.07.013
• 作为产物：
  描述：

  邻苯二胺 在 盐酸 、 potassium carbonate 作用下， 以 水 为溶剂， 反应 26.0h， 生成 2-((1H-benzimidazol-2-yl)ethyl)pyridin-2-ylmethyleneamine
  参考文献：
  名称：

  镉 (II) 与苯并咪唑的卤化物/伪卤化物配合物：合成、晶体结构和荧光特性

  摘要：

  摘要 两种新的双核 Cd(II) 配合物 [CdL1Cl2]2·H2O (1) 和 [CdL1(N3)2]2·CH3OH (2) 和一种双氰胺桥连一维多核网络 [CdL1(μ1,5-dca) )dca]n (3) 的潜在三齿 NNN 供体希夫碱 2-((1H-苯并咪唑-2-基-乙基亚氨基)-甲基)-吡啶 (L1) 和另一个双核 Cd(II) 复合物 [CdL2Cl(dca) ]2 (4) 类似的 NNN 供体席夫碱配体 2-((1H-苯并咪唑-2-基-丙基亚氨基)-甲基)-吡啶 (L2)，已合成并通过元素分析、IR 和单晶 X 表征-射线晶体学。配体L1和L2分别是吡啶-2-甲醛与2-氨基乙基-1H-苯并咪唑和2-氨基丙基-1H-苯并咪唑的[1+1]缩合产物。在配合物 1 和 4 中，两个 Cd(II) 中心由桥连的氯配体结合在一起，而在 2 中，两个 Cd(II) 中心由 μ1,1-叠氮化物离子桥接。配合物

  DOI：

  10.1016/j.molstruc.2017.07.013

文献信息

• Mitochondria‐Targeted Photoinduced Anticancer Activity of Oxidovanadium(IV) Complexes of Curcumin in Visible Light
  作者：Puja Prasad、Ila Pant、Imran Khan、Paturu Kondaiah、Akhil R. Chakravarty

  DOI：10.1002/ejic.201402001

  日期：2014.5

  Oxidovanadium(IV) complexes VO(py-aebmz)(B)]Cl (1, 2) and VO(napth-py-aebmz)(cur)]Cl 3; py-aebmz = 2-(1H-benzimidazol-2-yl)-N-(pyridin-2-ylmethylene)ethanamine, HB = acetylacetone (Hacac, 1) and curcumin (Hcur, 2), napth-py-aebmz = naphthalimide conjugated to py-aebmz ] have been prepared, characterized and their photoinduced DNA cleavage activities and photocytotoxicities studied. Complexes 1-3 each

  氧化钒(IV)配合物VO(py-aebmz)(B)]Cl (1, 2)和VO(napth-py-aebmz)(cur)]Cl 3 ；py-aebmz = 2-(1H-benzimidazol-2-yl)-N-(pyridin-2-ylmethylene)ethanamine, HB = 乙酰丙酮 (Hacac, 1) 和姜黄素 (Hcur, 2),nath-py-aebmz = 萘二甲酰亚胺已经制备、表征了与 py-aebmz 结合的 dna 分子，并研究了它们的光诱导 DNA 裂解活性和光细胞毒性。配合物 1-3 各自在 dmf/0.1 M tbap 中显示出 V-IV/V-III 氧化还原对在 -0.85 V 与 SCE 左右的不可逆循环伏安响应。该复合物通过羟基自由基和单线态氧途径在 454、530 和 647 nm 的可见光下显示出 DNA 光裂解活性。
• Copper(ii) complexes with 2NO and 3N donor ligands: synthesis, structures and chemical nuclease and anticancer activities
  作者：Chandrasekaran Rajarajeswari、Rangasamy Loganathan、Mallayan Palaniandavar、Eringathodi Suresh、Anvarbatcha Riyasdeen、Mohamad Abdulkadhar Akbarsha

  DOI：10.1039/c3dt32992e

  日期：——

  A series of water soluble copper(II) complexes of the types [Cu(L)Cl] 1–2, where LH is 2-(2-(1H-benzimidazol-2-yl)ethyliminomethyl)phenol (H(L1)), and 2-(2-(1H-benzimidazol-2-yl)-ethyliminomethyl)-4-methylphenol (H(L2)), and [Cu(L)Cl2] 3–6, where L is (2-pyridin-2-yl-ethyl)pyridin-2-ylmethyleneamine (L3), 2-(1H-benzimidazol-2-yl)ethylpyridin-2-yl-methyleneamine (L4), 2-(1H-benzimidazol-2-yl)ethyl(1H-imidazol-2-ylmethylene)amine (L5), and 2-(1H-benzimidazol-2-yl)ethyl-(4,4a-dihydroquinolin-2-ylmethylene)amine (L6), have been isolated and characterized by elemental analysis, electronic absorption, ESI-MS and EPR spectral techniques and the electrochemical method. The single crystal X-ray structures of [Cu(L1)Cl] 1 and [Cu(L2)Cl] 2 possess a distorted square-based coordination geometry while [Cu(L4)Cl2] 4 and [Cu(L6)Cl2] 6 possess a distorted trigonal bipyramidal coordination geometry. Both absorption spectral titration and an EthBr displacement assay reveal that all the complexes bind with calf thymus (CT) DNA through covalent mode of DNA interaction involving the replacement of an easily removable chloride ion with DNA nucleobases. All the complexes exhibit oxidative cleavage of supercoiled (SC) plasmid DNA in the presence of hydrogen peroxide as an activator. It is remarkable that at 50 μM concentration 5 and 6 completely degrade SC DNA into undetectable minor fragments and thus they act as efficient chemical nucleases. All the complexes are remarkable in displaying cytotoxicity against the HBL-100 human breast cancer cell line with potency more than that of the widely used drug cisplatin and hence they have the potential to act as promising anticancer drugs. Interestingly, they are non-toxic to normal cell lymphocytes isolated from human blood samples, revealing that they are selective in killing only the cancer cells.

  一系列[Cu(L)Cl] 1-2 型水溶性铜(II)络合物，其中 LH 为 2-(2-(1H-苯并咪唑-2-基)乙基亚氨基甲基)苯酚 (H(L1))、和 2-(2-(1H-苯并咪唑-2-基)乙基亚氨基甲基)-4-甲基苯酚 (H(L2))，以及 [Cu(L)Cl2] 3-6，其中 L 是 (2-吡啶-2-基-乙基)吡啶-2-基亚甲基胺 (L3)、2-(1H-苯并咪唑-2-基)乙基吡啶-2-基亚甲基胺（L4）、2-(1H-苯并咪唑-2-基)乙基(1H-咪唑-2-基亚甲基)胺（L5）和 2-(1H-苯并咪唑-2-基)乙基-(4、L6），并通过元素分析、电子吸收、ESI-MS 和 EPR 光谱技术以及电化学方法对其进行了表征。[Cu(L1)Cl]1和[Cu(L2)Cl]2的单晶X射线结构具有扭曲的正方形配位几何，而[Cu(L4)Cl2]4和[Cu(L6)Cl2]6则具有扭曲的三叉双锥配位几何。吸收光谱滴定法和 EthBr 置换测定法都表明，所有配合物都是通过共价 DNA 作用模式与小牛胸腺 DNA 结合的，其中涉及将易于移除的氯离子与 DNA 核碱基置换。在过氧化氢作为激活剂的情况下，所有复合物都能氧化切割超卷曲（SC）质粒 DNA。值得注意的是，在 50 μM 浓度下，5 号和 6 号复合物能将 SC DNA 完全降解为检测不到的小片段，因此它们是高效的化学核酸酶。所有复合物对 HBL-100 人类乳腺癌细胞系都具有显著的细胞毒性，其效力超过了广泛使用的顺铂，因此它们有可能成为有前途的抗癌药物。有趣的是，它们对从人体血液样本中分离出来的正常细胞淋巴细胞没有毒性，这表明它们只选择性地杀死癌细胞。
• Synthesis, crystal structure and magnetic characterization of a dinuclear Mn(II) complex with double end-on azide ligands
  作者：Hong-Yan Wu、Hui-Qin An、Bao-Lin Zhu、Shu-Rong Wang、Shou-Min Zhang、Shi-Hua Wu、Wei-Ping Huang

  DOI：10.1016/j.inoche.2007.06.018

  日期：2007.10

  A new dinuclear manganese(II) complex [MnL(N-3)(2)](2) center dot 2CH(3)OH 1 has been synthesized and characterized crystallographically and magnetically. L is a tridentate Schiff base ligand which is derived from the reaction of pyridine-2-carbaldehyde and 2-aminoethylbenzimidazole. In the complex 1, each Mn(II) ion is coordinated by one L, one terminal azide ligand and symmetrical double end-on bridging azide ligands. The intermolecular hydrogen bonds extend the structure into a two-dimensional layer. Magnetic determination of I indicates that ferromagnetic exchange interaction between the two manganese(II) ions exist in this complex through the double end-on azide bridges. (c) 2007 Elsevier B.V. All rights reserved.
• Mixed ligand copper(II) complexes of 1,10-phenanthroline with tridentate phenolate/pyridyl/(benz)imidazolyl Schiff base ligands: Covalent vs non-covalent DNA binding, DNA cleavage and cytotoxicity
  作者：Chandrasekaran Rajarajeswari、Mani Ganeshpandian、Mallayan Palaniandavar、Anvarbatcha Riyasdeen、Mohammad Abdulkadher Akbarsha

  DOI：10.1016/j.jinorgbio.2014.07.016

  日期：2014.11

  A series of copper(II) complexes of the types [Cu(L)(phen)]ClO4) 1-2, where HL is a tridentate ligand with two nitrogen and one oxygen donor atoms (2NO) such as 2-(2-(1H-benzimidazol-2-yl)ethyliminomethyl) phenol (HL1) and 2-(2-(1H-benzimidazol-2-yl)ethyl-imino)methyl)-4-methylphenol (HL2), phen is 1,10-phenanthroline and [Cu(L)(phen)](ClO4)(2) 3-6, where L is a tridentate ligand with three nitrogen donor atoms (3N) such as (2-pyridin-2-ylethyl)pyridin-2-ylmethyleneamine (13), 2-(1H-benzimidazol-2-yl)ethyl)-pyridin-2-yl-methyleneamine (L4), 2-(1H-benzimidazol-2-yl)ethyl)(1H-imidazol-2-ylmethylene)-amine (L5) and 2(1H-benzimidazol-2-yflethyl)(4,4a-dihydroquinolin-2-ylmethylene)amine (L6), has been isolated and characterized by different spectral techniques. In single crystal X-ray structures, 1 possesses square pyramidal distorted trigonal bipyramidal (SPDTBP), geometry whereas 3 and 4 possess trigonal bipyramidal distorted square pyramidal (TBDSP) geometry. UV-Vis and fluorescence spectral studies reveal that the complexes 1-6 bind non-covalently to calf thymus DNA more strongly than the corresponding covalently bound chlorido complexes [Cu(2NO)Cl] 1a-2a and [Cu(3N)Cl-2] 3a-6a. On prolonged incubation, all the complexes 1-6 exhibit double strand cleavage of supercoiled (SC) plasmid DNA in the absence of an activator. Also, they exhibit cytotoxicity against human breast cancer cell lines (HBL-100) more potent than their corresponding chlorido complexes 1a-6a, and have the potential to act as efficient cytotoxic drugs. (C) 2014 Elsevier Inc. All rights reserved.
• Halide/pseudohalide complexes of cadmium(II) with benzimidazole: Synthesis, crystal structures and fluorescence properties
  作者：Hai-Yan Zhao、Fu-Li Yang、Na Li、Xiao-Jing Wang

  DOI：10.1016/j.molstruc.2017.07.013

  日期：2017.11

  IR and single crystal X-ray crystallography. The ligands L1 and L2 are [1 + 1] condensation products of pyridine-2-carbaldehyde with 2-aminoethyl-1H-benzimidazole and 2-aminopropyl-1H-benzimidazole, respectively. In the complexes 1 and 4 the two Cd(II) centers are held together by the bridged chloride ligands, while in 2 the two Cd(II) centers are bridged by μ1,1-azide ions. Complex 3 has a one-dimensional

  摘要 两种新的双核 Cd(II) 配合物 [CdL1Cl2]2·H2O (1) 和 [CdL1(N3)2]2·CH3OH (2) 和一种双氰胺桥连一维多核网络 [CdL1(μ1,5-dca) )dca]n (3) 的潜在三齿 NNN 供体希夫碱 2-((1H-苯并咪唑-2-基-乙基亚氨基)-甲基)-吡啶 (L1) 和另一个双核 Cd(II) 复合物 [CdL2Cl(dca) ]2 (4) 类似的 NNN 供体席夫碱配体 2-((1H-苯并咪唑-2-基-丙基亚氨基)-甲基)-吡啶 (L2)，已合成并通过元素分析、IR 和单晶 X 表征-射线晶体学。配体L1和L2分别是吡啶-2-甲醛与2-氨基乙基-1H-苯并咪唑和2-氨基丙基-1H-苯并咪唑的[1+1]缩合产物。在配合物 1 和 4 中，两个 Cd(II) 中心由桥连的氯配体结合在一起，而在 2 中，两个 Cd(II) 中心由 μ1,1-叠氮化物离子桥接。配合物