2-(2-(1H-benzimidazol-2-yl)ethyliminomethyl)phenol | 905969-63-3

• 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-(2-(1H-benzimidazol-2-yl)ethyliminomethyl)phenol
• 英文别名: 2-[2-(1H-benzimidazol-2-yl)ethyliminomethyl]phenol
• CAS: 905969-63-3
• 化学式: C₁₆H₁₅N₃O
• 分子量: 265.315
• InChiKey: URXTXGNYZQIDAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  61.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  bis(acetylacetonate)oxovanadium 、 2-(2-(1H-benzimidazol-2-yl)ethyliminomethyl)phenol 以 甲醇 为溶剂， 以63%的产率得到[VO(acetylacetonato)(sal-aebmz)]
  参考文献：
  名称：

  钒与苯并咪唑衍生的ONN供体配体的模型钒（IV，V）配合物的合成，表征，反应性和催化潜力。

  摘要：

  [VO（acac）（2）]与ONN供体Schiff碱Hsal-ambmz（I）（Hsal-ambmz =通过水杨醛和2-氨基甲基苯并咪唑缩合获得的Schiff碱）之间的反应导致形成络合物[V （IV）O（acac）（sal-ambmz）]（1），[V（V）O（2）（acac-ambmz）]（2）（Hacac-ambmz =源自乙酰丙酮和2-氨基甲基苯并咪唑的席夫碱） ，以及已知的络合物[V（IV）O（sal-phen）]（3）（H（2）sal-phen =来自水杨醛和邻苯二胺的席夫碱）。同样，[V（IV）O（acac）（sal-aebmz）]（7）已从与Hsal-aebmz（II）（水杨醛和2-氨基乙基苯并咪唑衍生的Hsal-aebmz）的反应中分离出来。空中氧化1和7的甲醇溶液/悬浮液得到二氧钒（V）络合物[V（V）O（2）（sal-ambmz）]（4）和[V（V）O（2）（sal- a

  DOI：

  10.1021/ic0604922
• 作为产物：
  描述：

  2-aminoethylbenzimidazole dihydrochloride 、 水杨醛 在 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以80%的产率得到2-(2-(1H-benzimidazol-2-yl)ethyliminomethyl)phenol
  参考文献：
  名称：

  Copper(ii) complexes with 2NO and 3N donor ligands: synthesis, structures and chemical nuclease and anticancer activities

  摘要：

  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。

  DOI：

  10.1039/c3dt32992e

文献信息

• Mn(III) complexes of the monoprotic tridentate ONN donor 2-[2-(1H-(benzo[d]imidazol-2-yl)ethylimino)methyl]phenol as a functional mimic of haloperoxidase
  作者：Mannar R. Maurya、Priyanka Saini、Chanchal Haldar、Fernando Avecilla

  DOI：10.1016/j.poly.2012.07.095

  日期：2012.10

  The reaction of Mn-II(ClO4)(2) with 2-[2-(1H-(benzo[d]imidazol-2-yl)ethylimino)methyl]phenol (Hsalaebmz, I) under aerobic conditions results in the formation of [Mn-III(sal-aebmz)(2)]center dot ClO4 (1). In the presence of triethylamine and using MnCl2 under aerobic conditions. I forms [Mn-III(sal-aebmz-H)(sal-aebmz)] (2). These complexes are characterised on the basis of elemental and electrochemical analyses, spectroscopic (IR and UV-Vis) data and thermogravimetric studies. Single crystal X-ray analysis of 2 shows that it is stabilized in the solid state through intermolecular hydrogen bonding between the NH groups of the two benzimidazole moieties after losing one of the hydrogen atoms: the coordination sites of the ligand are the imine nitrogen of the benzimidazole ring, the azomethine nitrogen and the deprotonated phenolic oxygen. Complex 2 catalyses the oxidative bromination of styrene by H2O2, yielding 1,2-dibromo-1-phenylethane, 1-phenylethane-1,2-diol and 2-bromo-1 -phenylethane-1-ol, acting as a functional mimic of haloperoxidases. (C) 2012 Elsevier Ltd. 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.
• Kumar, Robin; Mahiya, Kuldeep; Mathur, Pavan, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2011, vol. 50, # 6, p. 775 - 780
  作者：Kumar, Robin、Mahiya, Kuldeep、Mathur, Pavan

  DOI：——

  日期：——
• Synthesis, Characterization, Reactivity, and Catalytic Potential of Model Vanadium(IV, V) Complexes with Benzimidazole-Derived ONN Donor Ligands
  作者：Mannar R. Maurya、Amit Kumar、Martin Ebel、Dieter Rehder

  DOI：10.1021/ic0604922

  日期：2006.7.1

  and 10 lead to (reversible) protonation of the bemzimidazole, while 8 was converted to an oxo-hydroxo species. Complexes 2, 4, and 8 catalyze the oxidation of methyl phenyl sulfide to methyl phenyl sulfoxide and methyl phenyl sulfone, a reaction mimicking the sulfideperoxidase activity of vanadate-dependent haloperoxidases. These complexes are also catalytically active in the oxidation of styrene to styrene

  [VO（acac）（2）]与ONN供体Schiff碱Hsal-ambmz（I）（Hsal-ambmz =通过水杨醛和2-氨基甲基苯并咪唑缩合获得的Schiff碱）之间的反应导致形成络合物[V （IV）O（acac）（sal-ambmz）]（1），[V（V）O（2）（acac-ambmz）]（2）（Hacac-ambmz =源自乙酰丙酮和2-氨基甲基苯并咪唑的席夫碱） ，以及已知的络合物[V（IV）O（sal-phen）]（3）（H（2）sal-phen =来自水杨醛和邻苯二胺的席夫碱）。同样，[V（IV）O（acac）（sal-aebmz）]（7）已从与Hsal-aebmz（II）（水杨醛和2-氨基乙基苯并咪唑衍生的Hsal-aebmz）的反应中分离出来。空中氧化1和7的甲醇溶液/悬浮液得到二氧钒（V）络合物[V（V）O（2）（sal-ambmz）]（4）和[V（V）O（2）（sal- a
• 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。