N-(2-Oxy-benzyl)-o-phenylendiamin | 7229-53-0

• 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-Oxy-benzyl)-o-phenylendiamin
• 英文别名: 2-(2-Amino-anilinomethyl)-phenol；N-(2-hydroxybenzyl)-o-phenylenediamine；2-[(2-Aminoanilino)methyl]phenol
• CAS: 7229-53-0
• 化学式: C₁₃H₁₄N₂O
• 分子量: 214.267
• InChiKey: PARUQVNBVVOVQQ-UHFFFAOYSA-N

物化性质

• 熔点：
  155-157 °C
• 沸点：
  411.3±30.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  58.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  chloroacetic acid imino ether hydrochloride 、 N-(2-Oxy-benzyl)-o-phenylendiamin 以 氯仿 为溶剂， 生成 2-chloromethyl-1-(2-hydroxybenzyl)-benzimidazole
  参考文献：
  名称：

  Benzimidazole derivatives and process for the production thereof

  摘要：

  Benzimidazoles的化学式为##STR1##，其中R.sub.1为o-羟基苯基、p-氯苯基或p-氟苯基，R.sub.2为2-4个碳原子的烷基，以及其生理上可接受的酸盐具有局部抗炎活性。

  公开号：

  US04011322A1
• 作为产物：
  描述：

  2-((2-aminophenylimino)methyl)phenol 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 3.0h， 以88%的产率得到N-(2-Oxy-benzyl)-o-phenylendiamin
  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

• Paal; Reckleben, Chemische Berichte, 1895, vol. 28, p. 934
  作者：Paal、Reckleben

  DOI：——

  日期：——
• 3-AMINO-2-AMINOMETHYLPHENOL DERIVATIVES AND COLORANTS COMPRISING THESE COMPOUNDS
  申请人：Wella Aktiengesellschaft

  公开号：EP1846361A2

  公开（公告）日：2007-10-24
• US4011322A
  申请人：——

  公开号：US4011322A

  公开（公告）日：1977-03-08
• [EN] 3-AMINO-2-AMINOMETHYLPHENOL DERIVATIVES AND COLORANTS COMPRISING THESE COMPOUNDS<br/>[FR] DERIVES DE 3-AMINO-2-AMINOMETHYLPHENOL ET COLORANTS CONTENANT CES COMPOSES
  申请人：PROCTER & GAMBLE

  公开号：WO2006086374A2

  公开（公告）日：2006-08-17

  [EN] 3-Amino-2-aminomethylphenol derivatives of the general formula (I) or physiologically compatible, water-soluble salts thereof, and agent comprising these compounds for the oxidative coloring of keratin fibers.
  [FR] L'invention porte sur des dérivés de 3-amino-2-aminomethylphenol représentés par la formule (I) ou sur des sels hydrosolubles de ceux-ci physiologiquement compatibles, ainsi que sur un agent contenant ces composés pour la coloration oxydante de fibres de kératine.
• 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.