N-(2-aminobenzylidene)benzene-1,2-diamine | 1126784-43-7

• 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-aminobenzylidene)benzene-1,2-diamine
• 英文别名: 2-[(2-aminophenyl)iminomethyl]aniline
• CAS: 1126784-43-7
• 化学式: C₁₃H₁₃N₃
• 分子量: 211.266
• InChiKey: JAKFOJPQWPBNJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 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：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-tetrapyridinedioxidorhenium(V) chloride 、 N-(2-aminobenzylidene)benzene-1,2-diamine 以 乙腈 为溶剂， 以36%的产率得到[rhenium(V)(N-(2-aminobenzylidene)benzene-1,2-diamine(-2H))2](ReO4)
  参考文献：
  名称：

  第一个无氧“3+3”铼（V）配合物的合成和晶体结构

  摘要：

  摘要 合成并表征了一种新的无氧铼(V)络盐[Re(L 3 ) 2 ](ReO 4 )(H 2 L 3 = N -(2-氨基亚苄基)苯-1,2-二胺)通过单晶 X 射线结构测定、IR 和 NMR 光谱。螯合物L 3 被配位为双阴离子三齿N , N , N -供体二酰胺亚胺。铼 (V) 离子以扭曲的三棱柱为中心。

  DOI：

  10.1016/j.inoche.2007.10.011
• 作为产物：
  描述：

  N-o-nitrobenzilidene-o-phenylenediamine 在 sodiumsulfide nonahydrate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以90%的产率得到N-(2-aminobenzylidene)benzene-1,2-diamine
  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

• 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.
• Synthesis and crystal structure of the first oxofree ‘3+3’ rhenium(V) complex
  作者：Irvin Booysen、Thomas I.A. Gerber、Eric Hosten、Peter Mayer

  DOI：10.1016/j.inoche.2007.10.011

  日期：2008.1

  Abstract A new oxofree rhenium(V) complex salt, [Re(L 3 ) 2 ](ReO 4 )(H 2 L 3 = N -(2-aminobenzylidene)benzene-1,2-diamine), has been synthesized and characterized by single crystal X-ray structure determination, IR and NMR spectroscopy. The chelates L 3 are coordinated as dianionic tridentate N , N , N -donor diamidoimines. The rhenium(V) ion is centered in a distorted trigonal prism.

  摘要 合成并表征了一种新的无氧铼(V)络盐[Re(L 3 ) 2 ](ReO 4 )(H 2 L 3 = N -(2-氨基亚苄基)苯-1,2-二胺)通过单晶 X 射线结构测定、IR 和 NMR 光谱。螯合物L 3 被配位为双阴离子三齿N , N , N -供体二酰胺亚胺。铼 (V) 离子以扭曲的三棱柱为中心。