(E)-2-((3-羟基亚苄基)氨基)苯酚 | 26213-36-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: (E)-2-((3-羟基亚苄基)氨基)苯酚
• 英文名称: (E)-2-((3-hydroxybenzylidene)amino)phenol
• 英文别名: 3-{[(2-hydroxyphenyl)imino]methyl}phenol；3-hydroxybenzylidene-2-hydroxyaniline；N-(m-hydroxybenzylidene)-o-hydroxyaniline
• CAS: 26213-36-5
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: PQKMAPANQMNEHB-NTEUORMPSA-N

物化性质

• 熔点：
  122.5-123.5 °C
• 沸点：
  448.3±30.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

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

• 作为产物：
  描述：

  间羟基苯甲醛 、 2-氨基苯酚 以 水 为溶剂， 反应 2.0h， 以77%的产率得到(E)-2-((3-羟基亚苄基)氨基)苯酚
  参考文献：
  名称：

  白藜芦醇亚胺类似物清除 DPPH、Galvinoxyl 和 ABTS 自由基

  摘要：

  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。

  DOI：

  10.3390/molecules21010127

文献信息

• 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.
• US4176198A
  申请人：——

  公开号：US4176198A

  公开（公告）日：1979-11-27
• US4187317A
  申请人：——

  公开号：US4187317A

  公开（公告）日：1980-02-05
• US4198349A
  申请人：——

  公开号：US4198349A

  公开（公告）日：1980-04-15