N-(2-hydroxybenzylidene)-2-amino-4-chlorobenzoic acid | 58469-79-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-hydroxybenzylidene)-2-amino-4-chlorobenzoic acid
• 英文别名: N-salicylidene-2-amino-5-chlorobenzoic acid；N-(4-chlorocarboxyphenyl)salicylideneimine；4-Chloro-2-[(2-hydroxyphenyl)methylideneamino]benzoic acid
• CAS: 58469-79-7
• 化学式: C₁₄H₁₀ClNO₃
• 分子量: 275.691
• InChiKey: ZIRSCPCXACXKSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxybenzylidene)-2-amino-4-chlorobenzoic acid 、 nickel(II) chloride hexahydrate 以 乙醇 为溶剂， 生成 bis(N-(2-hydroxybenzylidene)-2-amino-4-chlorobenzoato)nickel(II)
  参考文献：
  名称：

  Mononuclear metal complexes of organic carboxylic acid derivatives: Synthesis, spectroscopic characterization, thermal investigation and antimicrobial activity

  摘要：

  Two Schiff base ligands bearing organic acid moiety, vis., N-(2-thienylmethylidene)-2-amino-4-chlorobenzoic acid (HL1) and N-(2-hydroxybenzylidene)-2-amino-4-chlorobenzoic acid (H2L2) have been synthesized by the interaction of 2-thiophenecarboxaldehyde and 2-hydroxybenzaldehyde with 2-amino-4-chlorobenzoic acid. Co(II), Ni(II), Cu(II) and Zn(II) complexes of these ligands have been prepared. They are characterized on the basis of analytical data, molar conductance, IR, H-1 NMR, UV-vis, mass spectra, magnetic measurements, thermal analysis and X-ray powder diffraction technique. The molar conductance data reveal that these complexes are non-electrolytes. The ligands are coordinated to the metal ions in a terdentate manner with ONO/ONS donor sites of the carbonyl oxygen, azomethine nitrogen and phenolic oxygen or thiophenic sulphur. An octahedral structure is proposed for the prepared metal complexes and some ligand field parameters (D-q, B and beta) in addition to USE were calculated. The thermal stability of the metal complexes is evaluated. The Schiff base ligands and their metal complexes have been tested against four species of bacteria as well as four species of fungi and the results have been compared with some known antibiotics. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2006.05.038
• 作为产物：
  描述：

  水杨醛 、 2-氨基-5-氯苯甲酸 以 甲醇 为溶剂， 反应 4.0h， 以81%的产率得到N-(2-hydroxybenzylidene)-2-amino-4-chlorobenzoic acid
  参考文献：
  名称：

  NOO型三齿席夫碱配体及其一维Cu（II）配位聚合物：合成，晶体结构，生物大分子相互作用和自由基清除活性

  摘要：

  摘要合成了N-水杨基-2-氨基5-氯苯甲酸（H2L），NOO型三齿席夫碱及其一维Cu（II）配位聚合物[Cu2（H2L）2（MeOH）] n。通过CHN分析，FTIR，1H NMR，13C NMR，ESI-MS和XRD技术进行表征。已通过电子吸收和荧光光谱研究了H2L Schiff碱配体及其Cu（II）配位聚合物与生物大分子{小牛胸腺DNA（CT-DNA）和牛血清白蛋白（BSA）}的相互作用。实验结果表明，H2L Schiff碱配体及其Cu（II）配位聚合物通过中等插入模式与CT-DNA结合。此外，H2L Schiff碱配体与其Cu（II）配位聚合物和BSA之间的荧光猝灭机理是静态猝灭过程。使用DPPH和H2O2方法根据IC50确定H2L Schiff碱配体及其Cu（II）配位聚合物的自由基清除活性。在生物大分子相互作用和自由基活性研究中，发现Cu（II）配位聚合物比游离H2L Schiff碱配体提供更好的结果。

  DOI：

  10.1016/j.ica.2020.119994

文献信息

• Synthesis, characterization, DNA binding and cleavage properties of a ternary copper(II) Schiff base complex
  作者：Xin Li、Cai-Feng Bi、Yu-Hua Fan、Xia Zhang、Xiao-Dan Wei、Xiang-Min Meng

  DOI：10.1007/s11243-014-9836-7

  日期：2014.8

  A ternary coordination complex 2Cu(C14H8NO3Cl)(C12H8N2)·3CH3OH of a Schiff base (C14H8NO3Cl: 4-chloroanthranilic acid–salicylaldehyde) was synthesized from 4-chloroanthranilic acid, salicylaldehyde, copper acetate and 1,10-phenanthroline and characterized by physicochemical and spectroscopic methods. X-ray crystallography shows that the copper atom is five coordinated by the imine nitrogen, two nitrogen atoms from 1,10-phenanthroline, the hydroxyl oxygen and the carboxylate oxygen atom. The interaction of the complex with calf-thymus DNA was investigated by UV absorption spectroscopy, fluorescence emission spectroscopy and viscosity. In addition, the cleavage reaction with pBR322 supercoiled plasmid DNA was investigated. The complex binds to DNA and also exhibits significant DNA cleavage activity.

  以 4-氯邻苯二甲酸、水杨醛、醋酸铜和 1,10-菲罗啉为原料，合成了希夫碱（C14H8NO3Cl：4-氯邻苯二甲酸-水杨醛）的三元配位配合物 2Cu(C14H8NO3Cl)(C12H8N2)-3CH3OH，并利用理化和光谱方法对其进行了表征。X 射线晶体学显示，铜原子与亚胺氮、1,10-菲罗啉的两个氮原子、羟基氧和羧基氧原子配位。通过紫外吸收光谱、荧光发射光谱和粘度，研究了复合物与小牛胸腺 DNA 的相互作用。此外，还研究了与 pBR322 超卷曲质粒 DNA 的裂解反应。该复合物可与 DNA 结合，并具有显著的 DNA 裂解活性。
• Synthesis, characterization and anticancer activity of two ternary copper(ІІ) Schiff base complexes
  作者：Xin Li、Cheng Fang、Ziao Zong、Liansheng Cui、Caifeng Bi、Yuhua Fan

  DOI：10.1016/j.ica.2015.04.012

  日期：2015.6

  Two ternary copper(II) Schiff base complexes 2Cu(C14H8NO3F)(C12H8N2)center dot 3CH(3)OH (1) and 2Cu(C14H8NO3Cl)(C12H8N2)center dot 3CH(3)OH (2) were synthesized and characterized by IR spectroscopy, elemental analysis, and single crystal X-ray diffraction. X-ray crystallography shows that both of the copper atoms adopt square pyramidal geometry. Each copper atom is five coordinated by one nitrogen atom from -C=N-, two nitrogen atoms from 1,10-phenanthroline, one hydroxyl oxygen atom and one carboxylate oxygen atom. The proteasome is often found to be overactive in cancer cells. It has also been found that cancer cells are more sensitive to proteasome inhibition than normal cells. Therefore proteasome inhibitors are pursued as antitumor drugs. The anticancer activity of the two complexes was studied. The results showed that complex (1) can significantly inhibit the cellular proliferation of human breast cancer MDA-MB-231 cells. In addition, it has proteasome-inhibitory activity in human breast cancer MDA-MB-231 cells. The inhibition of the tumor proteasomal activity resulted in the accumulation of ubiquitinated proteins and ubiquitinated form of I kappa B-alpha, (a natural proteasome substrate) followed by induction of apoptosis. The results suggest that the fluorine-containing copper complex, as a potent proteasome inhibitor, has potential to be developed into a novel anticancer drug. (C) 2015 Elsevier B.V. All rights reserved.
• Synthesis, characterization of a ternary Cu(II) Schiff base complex with degradation activity of organophosphorus pesticides
  作者：Xin Li、Dandan Zhang、Zihui Liu、Ying Xu、Dongfeng Wang

  DOI：10.1016/j.ica.2017.11.024

  日期：2018.2

  Organophosphorus pesticides are a class of the most important groups of insecticides and are widely applied to pest and plant diseases control in agriculture. The extensive application of organophosphorus pesticides can subsequently release organophosphorus pesticides into environment which may pose a seriously adverse impact to non-target organisms and humans. However, we could not ban organophosphorus pesticides at present as they are very efficient. Therefore, the new technique of degradation of organophosphorus pesticides must be studied. In this paper, a ternary copper Schiff base complex 2Cu (C14H8NO3Cl)(C12H8N2)center dot 3CH(3)OH was synthesized and characterised by physico-chemical and spectroscopic methods. The degraded effects of 4 pesticides by the complex were investigated. The results showed that the degraded rates of every organophosphorus pesticide were increased. However, the effects of degradation were varied because of the different molecule structures of organophosphorus pesticides. Gas chromatography-mass spectrometry (GC-MS) and ion chromatography were used to analyze the degradation products by the complex, and then the catalytic mechanism of degradation was proposed. The study results suggest that the Schiff base copper complex, as a potent catalyzer, may find its applications in catalytic degradation area. (C) 2017 Elsevier B.V. All rights reserved.