2-salicylidenamino-phenol; copper (II)-complex | 14039-58-8

• 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: 2-salicylidenamino-phenol; copper (II)-complex
• 英文别名: 2-Salicylidenamino-phenol; Kupfer(II)-Komplex；2-Salicylidenamino-phenol; Kupfer(II)-Salz；Copper;2-[(2-oxidophenyl)iminomethyl]phenolate
• CAS: 14039-58-8
• 化学式: C₁₃H₉NO₂*Cu
• 分子量: 274.766
• InChiKey: XTIHNIHYEHFELC-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  1.58
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-salicylidenamino-phenol; copper (II)-complex 在 氨 、 水 作用下， 以 甲醇 、 氨 为溶剂， 生成
  参考文献：
  名称：

  Pfeiffer, P.; Hesse, T.; Pfitzner, H., Journal fur praktische Chemie (Leipzig 1954), 1937, vol. 149, # 2, p. 217 - 296

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基苯酚 以 甲醇 、 aq. phosphate buffer 为溶剂， 反应 1.0h， 生成 2-salicylidenamino-phenol; copper (II)-complex
  参考文献：
  名称：

  Inhibition of copper-mediated aggregation of human γD-crystallin by Schiff bases

  摘要：

  Protein aggregation, due to the imbalance in the concentration of Cu2+ and Zn2+ ions is found to be allied with various physiological disorders. Copper is known to promote the oxidative damage of beta/gamma-crystallins in aged eye lens and causes their aggregation leading to cataract. Therefore, synthesis of a small-molecule 'chelator' for Cu2+ with complementary antioxidant effect will find potential applications against aggregation of beta/gamma-crystallins. In this paper, we have reported the synthesis of different Schiff bases and studied their Cu2+ complexation ability (using UV-Vis, FT-IR and ESI-MS) and antioxidant activity. Further based on their copper complexation efficiency, Schiff bases were used to inhibit Cu2+-mediated aggregation of recombinant human gamma D-crystallin (HGD) and beta/gamma-crystallins (isolated from cataractous human eye lens). Among these synthesized molecules, compound 8 at a concentration of 100 mu M had shown 95% inhibition of copper (100 mu M)-induced aggregation. Compound 8 also showed a positive cooperative effect at a concentration of 5-15 mu M on the inhibitory activity of human alpha A-crystallin (HAA) during Cu2+-induced aggregation of HGD. It eventually inhibited the aggregation process by additional 20%. However, 50% inhibition of copper-mediated aggregation of beta/gamma-crystallins (isolated from cataractous human eye lens) was recorded by compound 8 (100 mu M). Although the reductive aminated products of the imines showed better antioxidant activity due to their lower copper complexing ability, they were found to be non-effective against Cu2+-mediated aggregation of HGD.

  DOI：

  10.1007/s00775-016-1433-0

文献信息

• A Bridge Too Far: Testing the Limits of Polypyridyl Ligands in Bridging Soluble Subunits of a Coordination Polymer
  作者：Samuel V. F. Beddoe、Anthony J. Fitzpatrick、Jason R. Price、Neil Mallo、Jonathon E. Beves、Grace G. Morgan、Jonathan A. Kitchen、Tony D. Keene

  DOI：10.1021/acs.cgd.7b01256

  日期：2017.12.6

  Starting with a coordination polymer, [Cu(L)]2}n (1 where H2L = salicylidene-2-aminophenol), we have explored the ability of polypyridyl ligands (P) to bridge the monomer complex to form nine [Cu(L)]2(P)} complexes. The identity and solution stability of the [Cu(L)] units has been investigated through a novel combined UV–vis/EPR experiment and it has been found to be a stable supramolecular building

  从配位聚合物[Cu（L）] 2 } n（1其中H 2 L =水杨基-2-氨基苯酚）开始，我们探索了聚吡啶基配体（P）桥接单体络合物形成九种 [Cu（L）] 2（P）}络合物。[Cu（L）]单元的身份和溶液稳定性已通过新颖的UV-vis / EPR组合实验进行了研究，已发现它是用于构建离散配合物和配位聚合物的稳定的超分子建筑单元。[Cu（L）]单元通过添加4,4'-联吡啶显着改变了结构的连通性，并通过Cu（II）轨道的重新定向改变了反铁磁相互作用的强度。我们还介绍了1的结构，即首次报道其合成后的80年。
• Electrochemical synthesis and structural characterization of nickel(II) and copper(II) complexes of tridentate schiff bases: Molecular structure of the five-coordinated copper(II) complex: 1,10-phenanthroline {2-[(2-oxyphenyl)iminomethyl]phenolato}copper(II)
  作者：Elena Labisbal、Jose A. Garcia-Vazquez、Jaime Romero、Sofia Picos、Antonio Sousa、Alfonso Castiñeiras、Cäcilia Maichle-Mössmer

  DOI：10.1016/0277-5387(94)00292-m

  日期：1995.3

  of metal anodes (copper and nickel) in acetonitrile solutions of Schiff bases (H2L) (synthesized from salicylaldehydes and 2-aminophenols) gave CuL and NiL complexes. When 1,10-phenanthroline (phen) or 2,2′-bipyridine (bipy) was added to the electrolytic cell, the mixed complexes CuLL′ and NiLL′ (L′ = phen or bipy) were obtained. The crystal structure of 1,10-phenanthroline 2-[(2-oxyphenyl)iminomet

  摘要在由水杨醛和2-氨基苯酚合成的席夫碱（H2L）的乙腈溶液中，金属阳极（铜和镍）的电化学氧化产生了CuL和NiL配合物。当将1，10-菲咯啉（phen）或2，2′-联吡啶（bipy）添加到电解池中时，获得混合的配合物CuLL′和NiLL′（L′＝ phen或bipy）。通过X射线衍射测定1，10-菲咯啉2-[（（2-氧苯基）亚氨基甲基]苯酚基}铜（II）的晶体结构。该结构由单体分子组成，其中铜原子具有扭曲的方金字塔形CuN3O2核。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Cu: MVol.B4, 165, page 1813 - 1815
  作者：

  DOI：——

  日期：——
• Inhibition of copper-mediated aggregation of human γD-crystallin by Schiff bases
  作者：Priyanka Chauhan、Sai Brinda Muralidharan、Anand Babu Velappan、Dhrubajyoti Datta、Sanjay Pratihar、Joy Debnath、Kalyan Sundar Ghosh

  DOI：10.1007/s00775-016-1433-0

  日期：2017.6

  Protein aggregation, due to the imbalance in the concentration of Cu2+ and Zn2+ ions is found to be allied with various physiological disorders. Copper is known to promote the oxidative damage of beta/gamma-crystallins in aged eye lens and causes their aggregation leading to cataract. Therefore, synthesis of a small-molecule 'chelator' for Cu2+ with complementary antioxidant effect will find potential applications against aggregation of beta/gamma-crystallins. In this paper, we have reported the synthesis of different Schiff bases and studied their Cu2+ complexation ability (using UV-Vis, FT-IR and ESI-MS) and antioxidant activity. Further based on their copper complexation efficiency, Schiff bases were used to inhibit Cu2+-mediated aggregation of recombinant human gamma D-crystallin (HGD) and beta/gamma-crystallins (isolated from cataractous human eye lens). Among these synthesized molecules, compound 8 at a concentration of 100 mu M had shown 95% inhibition of copper (100 mu M)-induced aggregation. Compound 8 also showed a positive cooperative effect at a concentration of 5-15 mu M on the inhibitory activity of human alpha A-crystallin (HAA) during Cu2+-induced aggregation of HGD. It eventually inhibited the aggregation process by additional 20%. However, 50% inhibition of copper-mediated aggregation of beta/gamma-crystallins (isolated from cataractous human eye lens) was recorded by compound 8 (100 mu M). Although the reductive aminated products of the imines showed better antioxidant activity due to their lower copper complexing ability, they were found to be non-effective against Cu2+-mediated aggregation of HGD.
• Pfeiffer, P.; Hesse, T.; Pfitzner, H., Journal fur praktische Chemie (Leipzig 1954), 1937, vol. 149, # 2, p. 217 - 296
  作者：Pfeiffer, P.、Hesse, T.、Pfitzner, H.、Scholl, W.、Thielert, H.

  DOI：——

  日期：——