2-((2-(piperazin-1-yl)ethylimino)methyl)-4-bromophenol | 639452-69-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-((2-(piperazin-1-yl)ethylimino)methyl)-4-bromophenol
• 英文别名: 4-Bromo-2-(2-piperazin-1-ylethyliminomethyl)phenol
• CAS: 639452-69-0
• 化学式: C₁₃H₁₈BrN₃O
• 分子量: 312.209
• InChiKey: CRQODJRLGCKDJV-UHFFFAOYSA-N

物化性质

• 沸点：
  437.1±45.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-((2-(piperazin-1-yl)ethylimino)methyl)-4-bromophenol 、 zinc(II) chloride 以 甲醇 为溶剂， 反应 8.0h， 以83.1%的产率得到Zn(2-((2-(piperazin-1-yl)ethylimino)methyl)-4-bromophenol)Cl2
  参考文献：
  名称：

  Mononuclear zinc(II) complexes of 2-((2-(piperazin-1-yl)ethylimino)methyl)-4-substituted phenols: Synthesis, structural characterization, DNA binding and cheminuclease activities

  摘要：

  Four new new zinc(II) complexes [Zn(HL1-4)Cl-2] (1-4), where HL1-4 = 2-((2-(piperazin-1-yl)ethylimino)methyl)-4-substituted phenols, have been isolated and fully characterized using various spectro-analytical techniques. The X-ray crystal structure of complex 4 shows the distorted trigonal-bipyramidal coordination geometry around zinc(II) ion. The crystal packing is stabilized by intermolecular N-H center dot center dot center dot O hydrogen bonding interaction. The complexes display no d-d electronic band in the visible region due to d(10) electronic configuration of zinc(II) ion. The electrochemical properties of the synthesized ligands and their complexes exhibit similar voltammogram at reduction potential due to electrochemically innocent Zn(II) ion, which evidenced that the electron transfer is due to the nature of the ligand. Binding interaction of complexes with calf thymus DNA was studied by UV-Vis absorption titration, viscometric titration and cyclic voltammetry. All complexes bind with CT DNA by intercalation, giving the binding affinity in the order of 2 > 1 >> 3 > 4. The prominent cheminuclease activity of complexes on plasmid DNA (pBR322 DNA) was observed in the absence and presence of H2O2. Oxidative pathway reveals that the underlying mechanism involves hydroxyl radical. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2014.01.026
• 作为产物：
  描述：

  N-氨乙基哌嗪 、 5-溴水杨醛 以 甲醇 为溶剂， 生成 2-((2-(piperazin-1-yl)ethylimino)methyl)-4-bromophenol
  参考文献：
  名称：

  新型氯桥酚盐配合物的磁结构相关性，抗氧化剂，DNA相互作用和生长抑制活性†

  摘要：

  由4-取代-2-（（2-（哌嗪-1-基）乙基亚氨基）甲基）苯酚合成了一类新型的氯桥联双核镍（II）和铜（II）酚盐配合物（1-8）。 L 1-4）和特征。配合物4和8的XRD分析表明，两个单核单元通过桥连的氯原子相连，从而产生了双核配合物。配合物的稳定性已使用分光光度法确定。配合物5–8对DPPH自由基具有显着的抗氧化活性。对复合物与CT-DNA的结合研究表明，部分插入/静电相互作用，对pBR322 DNA的裂解能力表明，羟基自由基作为裂解反应的中间体。该IC 50复合物的值2，6和8抵靠的HepG2细胞系是用顺铂的可比性。为了发现核染色质的裂解程度，采用了碘化丙锭染色和彗星试验。在新合成的配合物中，铜（II）配合物与其镍（II）类似物相比具有更好的生物活性。

  DOI：

  10.1039/c4ra06941b

文献信息

• Equilibrium Studies in Solution Involving Nickel(II) Complexes of Flexidentate Schiff Base Ligands:  Isolation and Structural Characterization of the Planar Red and Octahedral Green Species Involved in the Equilibrium
  作者：Suman Mukhopadhyay、Debdas Mandal、Dipesh Ghosh、Israel Goldberg、Muktimoy Chaudhury

  DOI：10.1021/ic0346174

  日期：2003.12.1

  flexidentate 5-substituted salicylaldimino Schiff base ligands (L1-OH-L3-OH) based on 1-(2-aminoethyl)piperazine (X=H, L1-OH; X=NO2, L2-OH; and X=Br, L3-OH) and their nickel(II) complexes (1a, 1b, 2, and 3) have been reported. The piperazinyl arm of these ligands can in principle have both boat and chair conformations that allow the ligands to bind the Ni(II) center in an ambidentate manner, forming square-planar

  基于1-（2-氨基乙基）哌嗪（X = H，L1-OH; X = NO2，L2-OH;和X = Br）的三个新的flexidentate 5-取代的水杨基二氨基Schiff碱配体（L1-OH-L3-OH） ，L3-OH）及其镍（II）配合物（1a，1b，2和3）已被报道。这些配体的哌嗪基臂原则上可以具有船型和椅型构型，其允许配体以双齿方式结合Ni（II）中心，形成正方形-平面和/或八面体的配合物。水杨醛芳环中取代基的性质以及配合物中缔合阴离子的类型对分离产物的配位几何形状有深远的影响。与母体配体L1-OH一起，得到的产物是呈四苯基硼酸盐（1a）形式分离的平面红色化合物[Ni（L1-O）] +，或八面体绿色化合物[Ni（L1-NH）（H2O） 3]（2+），用硫酸根阴离子分离（1b）；两者均已在晶体学上进行了表征。在水溶液中，这些平面（S = 0）和八面体（S = 1）形式均处于平衡状态，使用Evans方法的方法，通过1H
• Solvent Mediated Hydrogen-bonded Supramolecular Network of a Cu(II) Complex Involving N₂O Donor Ligand and Terephthalate
  作者：Jishnunil Chakraborty

  DOI：10.5012/jkcs.2011.55.2.199

  日期：2011.4.20

  일차원 수소결합형 배위고분자 $[Cu^II}(C_13}H_17}N_3OBr)(C_8H_5O_4)]\cdot}2H_2O.CH_3OH$을 합성하여 단결정 X-선 회절 연구로 특성을 규명하였다. 단량체 단위는 사각평면의 중심 $Cu^II}$를 갖고 있다. 네개의 배위자리 중 세자리는 $N_2O$-주개 세트를 갖는 Schiff 염기형 리간드 (4-bromo-2-[(2-piperazin-1-yl-ethylimino)-methyl]-phenol)가 차지하고, 네 번째 자리는 옆에 있는 테레프탈레이트 단위의 산소 원자가 차지한다. 두개의 인접한 중성분자는 분자간 N-H---O 및 O-H---N 수소결합에 의해 연결되어 이합체 쌍을 형성한다. 각 이합체 쌍은 불연속적인 물 및 메탄올 분자에 의해 수소결합으로 다시 연결되어 일차원 초분자 네트워크를 형성한다. The title one-dimensional hydrogen-bonded coordination compound $[Cu^II}(C_13}H_17}N_3OBr)(C_8H_5O_4)]\cdot}2H_2O.CH_3OH$ has been synthesized and characterized by single crystal X-ray diffraction study. The monomeric unit contains a square-planar $Cu^II}$ centre. The four coordination sites are occupied by a tridentate anionic Schiff base ligand (4-bromo-2-[(2-piperazin-1-yl-ethylimino)-methyl]-phenol) which furnishes an $N_2O$-donor set, with the fourth position being occupied by the oxygen atom of an adjacent terephthalate unit. Two adjacent neutral molecules are linked through intermolecular N-H---O and O-H---N hydrogen bonds and generate a dimeric pair. Each dimeric pair is connected with each other via discrete water and methanol molecules by hydrogen bonding to form a one-dimensional supramolecular network.

  单晶的特性通过衍射研究来表征。单体单元的中心$Cu^II}$位于矩形平面内。四个配位位点中的三个是席夫碱型配体，具有 $N_2O$-供体组 (4-bromo-2-[(2-piperazin-1-yl-ethimino)-methyl]-苯酚）被占据，第四个位置被旁边的对苯二甲酸酯单元的氧原子占据。相邻的两个中性分子通过分子间N-H---O和O-H---N氢键连接形成二聚体对。每个二聚体对通过氢键与不连续的水和甲醇分子重新连接，形成一维超分子网络。 标题一维氢键配位化合物$[Cu^II}(C_13}H_17}N_3OBr)(C_8H_5O_4)] \cdot}2H_2O.CH_3OH$ 已被合成并通过单晶 X 射线衍射研究进行表征。单体单元包含一个方形平面 $Cu^II}$ 中心。四个配位位点被三齿阴离子席夫碱配体（4-溴-2-[(2-哌嗪-1-基-乙基亚氨基)-甲基]-苯酚）占据，提供 $N_2O$-供体组，第四个位置被相邻对苯二甲酸酯单元的氧原子占据。两个相邻的中性分子通过分子间N-H---O和O-H---N氢键连接并生成二聚体对。每个二聚体对通过离散的水和甲醇分子通过氢键相互连接，形成一维超分子网络。
• Antioxidant, DNA binding and nuclease activities of heteroleptic copper(II) complexes derived from 2-((2-(piperazin-1-yl)ethylimino)methyl)-4-substituted phenols and diimines
  作者：J. Ravichandran、P. Gurumoorthy、M.A. Imran Musthafa、A. Kalilur Rahiman

  DOI：10.1016/j.saa.2014.06.045

  日期：2014.12

  A series of heteroleptic copper(II) complexes of the type [CuL(1-4)(diimine)](ClO4)2 (1-8) [L(1-4)=2-((2-(piperazin-1-yl)ethylimino)methyl)-4-substituted phenols, and diimine=2,2'-bipyridyl (bpy) or 1,10-phenanthroline (phen)], have been synthesized and characterized by spectroscopic methods. The IR spectra of complexes indicate the presence of uncoordinated perchlorate anions and the electronic spectra

  [CuL（1-4）（diimine）]（ClO4）2（1-8）[L（1-4）= 2-（（2-（piperazin-1 -亚乙基）亚氨基）甲基）-4-取代的苯酚和二亚胺＝ 2,2'-联吡啶基（bpy）或1,10-菲咯啉（phen）]，并已通过光谱法表征。配合物的红外光谱表明存在未配位的高氯酸根阴离子，电子光谱揭示了在铜（II）核周围具有N4O配位环境的方形金字塔形几何结构。单核配合物的电化学研究表明，在阴极区域存在单电子不可逆还原波。g ||的配合物的EPR光谱 （2.206-2.214）和A || （154-172×10（-）（4）cm（-）（1））值支持基于正方形的CuN3O配位发色团和存在[公式：见文字]基态。针对DPPH的抗氧化剂研究显示了合成配合物的有效自由基清除性能。结合研究表明，杂配铜（II）配合物通过小沟和静电相互作用与小牛胸腺DNA（CT-DNA）相互作用，并且所有配合物均显示出明显的针对超螺旋pBR322
• Synthesis, Crystal Structures, and Urease Inhibitory Activities of Two Isostructural Schiff Base Cadmium(II) Complexes
  作者：Da-Hua Shi、Lin Zhang、Li-Li Ni、Shun Bai、Zhong-Lu You

  DOI：10.1080/15533174.2010.487057

  日期：2010.5.28

  Two isostructural cadmium(II) complexes, [Cd(L1)(NO3)2 (H2O)] center dot CH3OH (1) and [Cd(L2)(NO3)2(H2O)] center dot CH3OH (2), derived from the Schiff bases 4-bromo-2-[(2-piperazinylethylimino)methyl]phenol (L1) and 4-chloro-2-[(2-piperazinylethylimino)methyl]phenol (L2), respectively, were prepared and structurally characterized by X-ray diffraction. Each complex consists of a mononuclear cadmium(II) complex molecule and a methanol molecule of crystallization. The Cd atom in each complex is six-coordinated by one phenolate O, one imine N and one amine N atoms of the Schiff base ligand, two O atoms from two nitrate anions, and one water O atom, forming distorted octahedral coordination. The urease inhibitory activities of the complexes were evaluated.