(E)-2-(((3-hydroxyphenyl)imino)methyl)phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-2-(((3-hydroxyphenyl)imino)methyl)phenol
• 英文别名: 2-((E)-(3-hydroxyphenylimino)methyl)phenol；2-{[(3-hydroxyphenyl)imino]methyl}phenol；N-(o-hydroxybenzylidene)-m-hydroxyaniline
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: UALRWOGQNILXLJ-NTEUORMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.82
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-2-(((3-hydroxyphenyl)imino)methyl)phenol 、 diphenyl phosphite 以85%的产率得到
  参考文献：
  名称：

  AXMEDZADE, D. A.;SAXNOVSKAYA, E. B.;BABAEVA, S. G.;MUSTAFAEVA, S. K., AZERB. XIM. ZH., 1985, N 5, 69-72

  摘要：

  DOI：
• 作为产物：
  描述：

  水杨醛 、 3-氨基苯酚 以 乙醇 为溶剂， 反应 3.0h， 以48.68%的产率得到(E)-2-(((3-hydroxyphenyl)imino)methyl)phenol
  参考文献：
  名称：

  席夫碱配体金属配合物的制备、表征及生物活性筛选

  摘要：

  一种名为 (E)-2-(((3-hydroxyphenyl)imino)methyl)phenol (H2L) 的新型希夫碱配体是由 2-hydroxybenzaldehyde 与 3-aminophenol 以 1:1 的比例缩合而成。配体采用光谱技术进行表征。由 H2L 配体衍生的 La(III)、Er(III) 和 Yb(III) 复合物已经制备完成，并通过元素分析、红外光谱、电子光谱、质谱、摩尔电导率和热分析等常规技术对其进行了表征。红外光谱数据显示，H2L 配体通过偶氮甲基氮和两个去质子化的酚氧原子与金属离子配位，配位方式为双阴性三叉配位。配合物的热重分析数据显示，配合物中存在水合和配位水分子。评估了配体及其复合物对不同革兰氏阳性菌（金黄色葡萄球菌和枯草杆菌）、革兰氏阴性菌（沙门氏菌、大肠杆菌和绿脓杆菌）和真菌（曲霉菌和白色念珠菌）的抗菌和抗真菌活性。与配体相比，复合物对细菌和真菌具有更高的生物活性。讨论了希夫碱配体（H2L）与结肠癌（PDB 代码：2hq6）和肺癌（PDB 代码：1x2j）受体的结合能计算值。

  DOI：

  10.21608/ejchem.2021.68740.3515

文献信息

• The Scavenging of DPPH, Galvinoxyl and ABTS Radicals by Imine Analogs of Resveratrol
  作者：Peter Kotora、František Šeršeň、Juraj Filo、Dušan Loos、Juraj Gregáň、Fridrich Gregáň

  DOI：10.3390/molecules21010127

  日期：——

  Resveratrol (3,5,4′-trihydroxystilbene) is a phytoalexin produced by plants. Resveratrol is known for its anti-cancer, antiviral and antioxidant properties. We prepared imine analogs of resveratrol ((hydroxyphenyliminomethyl)phenols) and tested their antioxidant activity. All prepared resveratrol analogs were able to scavenge 2,2-diphenyl-1-picrylhydrazyl (DPPH), galvinoxyl radical (GOR) and 2,2′-

  白藜芦醇（3,5,4'-三羟基芪）是一种植物产生的植物抗毒素。白藜芦醇以其抗癌、抗病毒和抗氧化特性而闻名。我们制备了白藜芦醇（（羟苯基亚氨基甲基）酚类）的亚胺类似物并测试了它们的抗氧化活性。所有制备的白藜芦醇类似物都能够清除 2,2-二苯基-1-苦基肼 (DPPH)、加尔文氧基 (GOR) 和 2,2'-叠氮基-双(3-乙基苯并噻唑啉)-6-磺酸 (ABTS) 自由基。抗氧化活性效率与羟基的数量和位置相关。最有效的抗氧化剂是在其分子的亚苄基部分含有三个羟基的白藜芦醇类似物。这些结果为白藜芦醇类似物的化学结构和生物活性之间的关系提供了新的见解。
• Synthesis, characterization, and reactivity of Pd(II) salicylaldimine complexes derived from aminophenols
  作者：Bennett J Tardiff、Joshua C Smith、Stephen J Duffy、Christopher M Vogels、Andreas Decken、Stephen A Westcott

  DOI：10.1139/v07-036

  日期：2007.5.1

  of salicylaldehydes with 3- and 4-aminophenol, reacted with palladium(II) acetate to give the corresponding bis(N-arylsalicylaldiminato)palladium(II) complexes. These complexes have been found to be active catalysts for the Suzuki–Miyaura cross-coupling of aryl bromides and iodides with aryl boronic acids, using water as a solvent.Key words: cross-coupling, green chemistry, palladium, salicylaldimines

  席夫碱源自水杨醛与 3- 和 4- 氨基苯酚的缩合，与乙酸钯 (II) 反应生成相应的双 (N-芳基水杨醛基亚氨基) 钯 (II) 配合物。已发现这些配合物是芳基溴化物和碘化物与芳基硼酸的 Suzuki-Miyaura 交叉偶联的活性催化剂，以水为溶剂。 关键词：交叉偶联，绿色化学，钯，水杨醛亚胺，席夫碱，铃木-宫浦。
• Preparation, Characterization and Biological Activity Screening on Some Metal Complexes Based of Schiff Base Ligand
  作者：Adel Elsonbati、Moustafa Diab、S. ‌‌‌Y. Abbas S. ‌‌‌Y. Abbas、Gehad Mohamed、Shimaa Morgan

  DOI：10.21608/ejchem.2021.68740.3515

  日期：2021.4.18

  A novel Schiff base ligand named (E)-2-(((3-hydroxyphenyl)imino)methyl)phenol (H2L) was prepared through condensation of 2-hydroxybenzaldehyde with 3-aminophenol in1:1 ratio. The ligand was characterized using spectroscopic techniques. La(III), Er(III) and Yb(III) complexes derived from H2L ligand have been prepared and characterized by conventional techniques including elemental analyses, infrared, electronic spectra, mass spectra, molar conductivity and thermal analysis. IR spectral data showed that H2L ligand is coordinated to the metal ions in a bi-negative tridentate manner through the azomethine nitrogen and two deprotonated phenolic oxygen atoms. The thermogravimetric analysis data of the complexes displays the existence of hydrated and coordinated water molecules in the complexes. The ligand and its complexes were evaluated for their antibacterial and antifungal activities against different gram positive bacteria (Staphylococcus Aureus and Bacillis subtilis), gram negative bacteria (Salmonella SP., Escherichia Coli and Pseudomonas aeruginosa) and fungi (Aspergillus Fumigates and Candida albicans). The complexes were found to have higher biological activity against bacteria and fungi more than the ligand. The calculated binding energy values of the receptors of the colon cancer (PDB code: 2hq6) and the lung cancer (PDB code: 1x2j) for Schiff base ligand (H2L) were discussed.

  一种名为 (E)-2-(((3-hydroxyphenyl)imino)methyl)phenol (H2L) 的新型希夫碱配体是由 2-hydroxybenzaldehyde 与 3-aminophenol 以 1:1 的比例缩合而成。配体采用光谱技术进行表征。由 H2L 配体衍生的 La(III)、Er(III) 和 Yb(III) 复合物已经制备完成，并通过元素分析、红外光谱、电子光谱、质谱、摩尔电导率和热分析等常规技术对其进行了表征。红外光谱数据显示，H2L 配体通过偶氮甲基氮和两个去质子化的酚氧原子与金属离子配位，配位方式为双阴性三叉配位。配合物的热重分析数据显示，配合物中存在水合和配位水分子。评估了配体及其复合物对不同革兰氏阳性菌（金黄色葡萄球菌和枯草杆菌）、革兰氏阴性菌（沙门氏菌、大肠杆菌和绿脓杆菌）和真菌（曲霉菌和白色念珠菌）的抗菌和抗真菌活性。与配体相比，复合物对细菌和真菌具有更高的生物活性。讨论了希夫碱配体（H2L）与结肠癌（PDB 代码：2hq6）和肺癌（PDB 代码：1x2j）受体的结合能计算值。
• Design, synthesis and biological evaluation of imine resveratrol derivatives as multi-targeted agents against Alzheimer's disease
  作者：Su-Yi Li、Xiao-Bing Wang、Ling-Yi Kong

  DOI：10.1016/j.ejmech.2013.10.068

  日期：2014.1

  A series of imine resveratrol derivatives (1-20) have been designed, synthesized, and evaluated as multi-targeted compounds for the treatment of Alzheimer's disease (AD).In vitro studies show that most of the molecules exhibit a significant ability to inhibit self-induced and Cu2+-induced beta-amyloid (A beta(1-42)) aggregation, and to function as potential antioxidants and biometal chelators. In particular, compound 9 is a potential lead compound for AD treatment (for compound 9, IC50 = 14.1 mu M for the antioxidant activity using DPPH free radical method; 64.6% at 20 mu M for self-induced A beta aggregation). Moreover, it is capable of decreasing reactive oxygen species (ROS) induced by Cu-A beta and shows good neuroprotective effects in human SH-SY5Y neuroblastoma cells. Taken together, these results suggest that 9 might be a promising lead compound for AD treatment. (C) 2013 Elsevier Masson SAS. All rights reserved.
• The antioxidant effect of imine resveratrol analogues
  作者：Jing Lu、Chang Li、Yun-Feng Chai、De-Yu Yang、Cui-Rong Sun

  DOI：10.1016/j.bmcl.2012.06.026

  日期：2012.9

  Twenty five Imine resveratrol analogues (IRAs) were synthesized, replacing the C=C bond in resveratrol with C=N bond, as well as substitution modifications on aromatic rings. Radical scavenging activities against DPPH, along with singlet oxygen quenching capacities were evaluated, and further confirmed using density functional theory calculations (DFT). It was found that IRAs bearing ortho-OH on B ring have better radical scavenging activities against DPPH than resveratrol, these compounds were also found to be effective O-1(2) quenchers. Theoretical studies on the reaction mechanism of these compounds with O-1(2) suggest that the 1,3-addition to a double bond with a -OH group with the formation of allylic hydroperoxide is the most probable reaction route. (C) 2012 Elsevier Ltd. All rights reserved.