2-((2-(piperazin-1-yl)ethylimino)methyl)-4-chlorophenol | 1245707-53-2

• 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-chlorophenol
• 英文别名: 4-chloro-2-((2-(piperazin-1-yl)ethylimino)methyl)phenol；4-Chloro-2-[(2-piperazin-1-ylethylimino)methyl]phenol；4-chloro-2-(2-piperazin-1-ylethyliminomethyl)phenol
• CAS: 1245707-53-2
• 化学式: C₁₃H₁₈ClN₃O
• 分子量: 267.758
• InChiKey: OQIMJYHWVAVJRQ-UHFFFAOYSA-N

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-chlorophenol 、 zinc(II) chloride 以 甲醇 为溶剂， 反应 8.0h， 以81.9%的产率得到Zn(2-((2-(piperazin-1-yl)ethylimino)methyl)-4-chlorophenol)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-氯代水杨醛 以 甲醇 为溶剂， 生成 2-((2-(piperazin-1-yl)ethylimino)methyl)-4-chlorophenol
  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

• A family of ligand and anion dependent structurally diverse Cu(<scp>ii</scp>) Schiff-base complexes and their catalytic efficacy in an <i>O</i>-arylation reaction in ethanolic media
  作者：Tanmoy Maity、Debraj Saha、Susmita Bhunia、Paula Brandão、Soma Das、Subratanath Koner

  DOI：10.1039/c5ra14758a

  日期：——

  Catalytic O-arylation reactions have been studied by employing a variety of copper(ii) Schiff-base complexes under environmentally benign conditions.

  催化的O-芳基化反应已经通过使用各种铜（II）席夫碱配合物在环境友好条件下进行研究。
• A series of mononuclear nickel(II) complexes of Schiff-base ligands having N,N,O- and N,N,N-donor sites: Syntheses, crystal structures, solid state thermal property and catecholase-like activity
  作者：Averi Guha、Kazi Sabnam Banu、Sudhanshu Das、Tanmay Chattopadhyay、Ria Sanyal、Ennio Zangrando、Debasis Das

  DOI：10.1016/j.poly.2012.07.088

  日期：2013.3

  [NiL4(ClBz)(H2O)]·1.25(H2O) (4) have been synthesized via Schiff-base formation by condensation between 2-benzoylpyridine and N-(2-aminoethyl)pyrrolidine for L1, salicylaldehyde and N-(2-aminoethyl)piperazine (L2), 5-chlorosalicylaldehyde and N-(2-aminoethyl)piperazine (L3), and 5-chlorosalicylaldehyde and N-(2-aminoethyl)morpholine (L4). These complexes are comprehensively characterized via routine physicochemical

  摘要四种新的单核镍（II）配合物，即[NiL1（H2O）3]（NO3）2（1），[NiL2（ ）3]（ ）2（2），[NiL3（ ）3]（ ）2（3）和[NiL4（ClBz）（ ）]·1.25（ ）（4）通过席夫碱形成，通过2-苯甲酰基吡啶和N-（2-氨基乙基）吡咯烷之间的缩合反应合成L1，水杨醛N-（2-氨基乙基）哌嗪（L2），5-氯水杨醛和N-（2-氨基乙基）哌嗪（L3），5-氯水杨醛和N-（2-氨基乙基）吗啉（L4）。这些配合物通过常规物理化学技术以及单晶X射线结构分析得到全面表征。尽管所有的镍络合物都是单核的，但儿茶酚酶的活性却显示出明显的变化，这取决于金属中心周围的配位环境。衍生自相同胺的配合物2和3在配体系统上带有额外的正电荷，有助于底物与催化剂的相互作用，从而促进3,5-DTBC氧化为3,5-DTBQ。相反，尽管配合物1和4在活性上与镍取代的邻苯二酚
• Synthesis, Characterization, and Antibacterial Activity of Cobalt(II) and Zinc(II) Complexes with Schiff Bases
  作者：Jian-Nan Li

  DOI：10.1080/15533174.2012.750343

  日期：2013.8.9

  compounds of cobalt(II) and zinc(II) with Schiff bases 4-chloro-2-[(2-ethylaminoethylimino)methyl]phenol and 4-chloro-2-[(2-piperazin-1-ylethylimino)methyl]phenol, respectively, were synthesized. The characterization of the newly formed compounds was done by elemental analysis, IR spectra, molar electric conductibility, and single crystal X-ray determination. The Co atom in the cobalt complex is in an

  钴（II）和锌（II）与席夫碱4-氯-2-[（2-乙基氨基乙基亚氨基）甲基]苯酚和4-氯-2-[（2-哌嗪-1-基乙基亚氨基）甲基]苯酚的配位化合物分别合成。通过元素分析，红外光谱，摩尔电导率和单晶X射线测定对新形成的化合物进行表征。钴配合物中的Co原子为八面体配位，锌配合物中的Zn原子为四面体配位。已评估了席夫碱和两种复合物对四种革兰氏阳性细菌化脓性链球菌，无乳链球菌，金黄色葡萄球菌和炭疽杆菌的抗菌活性。，以及两种革兰氏阴性细菌，即肺炎克雷伯菌和铜绿假单胞菌。
• 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.