4,4'-(1,2-ethanediyldiimino)bis-(N-hydroxybenzenecarboximidamide) | 1193099-30-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4,4'-(1,2-ethanediyldiimino)bis-(N-hydroxybenzenecarboximidamide)
• 英文别名: N'-hydroxy-4-[2-[4-(N'-hydroxycarbamimidoyl)anilino]ethylamino]benzenecarboximidamide
• CAS: 1193099-30-7
• 化学式: C₁₆H₂₀N₆O₂
• 分子量: 328.374
• InChiKey: XVGIVZRVQVLJJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  141
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4'-(1,2-ethanediyldiimino)bis-(N-hydroxybenzenecarboximidamide) 在 10% palladium on carbon 、 甲酸铵 、 溶剂黄146 作用下， 反应 2.0h， 生成 1.2-Bis-<4-amidino-anilino>-ethan
  参考文献：
  名称：

  1,2-Ethane bis-1-amino-4-benzamidine is active against several brain insult and seizure challenges through anti-NMDA mechanisms targeting the 3H-TCP binding site and antioxidant action

  摘要：

  Five bis-benzamidines were screened towards murine magnesium deficiency-dependent audiogenic seizures, unravelling two compounds with efficacious doses 50 (ED50) less than 10 mg/kg. They were also screened against maximal electroshock and subcutaneous pentylenetetrazole-induced seizures, and explored for superoxide -scavenging activity. 1,2-Ethane bis-1-amino-4-benzamidine (EBAB) was selected and evaluated in 6 Hz seizure test (ED50 = 49 mg/kg) and at 4 mu g/kg in focal cerebral ibotenate poisoning in pups (sizes of both white and grey matter wounds were halved). EBAB was further tested on NMDA-induced seizures in mice (ED50 = 6 mg/kg) and on H-3-TC-binding to a rodent cerebral preparation (IC50 = 1.4 mu M). Taken as a whole, present data emphasise the suitability of bis-benzamidines as templates for designing brain protective compounds. (c) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.044
• 作为产物：
  描述：

  N,N'-bis(4-cyanophenyl)ethylenediamine 在 羟胺 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以87%的产率得到4,4'-(1,2-ethanediyldiimino)bis-(N-hydroxybenzenecarboximidamide)
  参考文献：
  名称：

  1,2-Ethane bis-1-amino-4-benzamidine is active against several brain insult and seizure challenges through anti-NMDA mechanisms targeting the 3H-TCP binding site and antioxidant action

  摘要：

  Five bis-benzamidines were screened towards murine magnesium deficiency-dependent audiogenic seizures, unravelling two compounds with efficacious doses 50 (ED50) less than 10 mg/kg. They were also screened against maximal electroshock and subcutaneous pentylenetetrazole-induced seizures, and explored for superoxide -scavenging activity. 1,2-Ethane bis-1-amino-4-benzamidine (EBAB) was selected and evaluated in 6 Hz seizure test (ED50 = 49 mg/kg) and at 4 mu g/kg in focal cerebral ibotenate poisoning in pups (sizes of both white and grey matter wounds were halved). EBAB was further tested on NMDA-induced seizures in mice (ED50 = 6 mg/kg) and on H-3-TC-binding to a rodent cerebral preparation (IC50 = 1.4 mu M). Taken as a whole, present data emphasise the suitability of bis-benzamidines as templates for designing brain protective compounds. (c) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.044

文献信息

• Bisbenzamidine derivatives for use as antioxidant
  申请人：Université de Mons-Hainaut

  公开号：EP2116236A1

  公开（公告）日：2009-11-11

  The invention is directed to the use of bisbenzamidine compounds of Formula (I) as antioxidant and as neuroprotective agents, wherein R1, R2, R3, R4 and L have the meaning defined in the claims.

  本发明涉及将式（I）的双苯基胍化合物用作抗氧化剂和神经保护剂，其中R1、R2、R3、R4和L的含义如权利要求所定义。
• 1,2-Ethane bis-1-amino-4-benzamidine is active against several brain insult and seizure challenges through anti-NMDA mechanisms targeting the 3H-TCP binding site and antioxidant action
  作者：Joseph Vamecq、Pierre Maurois、Nicole Pages、Pierre Bac、James P. Stables、Pierre Gressens、Dimitri Stanicki、Jean Jacques Vanden Eynde

  DOI：10.1016/j.ejmech.2010.03.044

  日期：2010.7

  Five bis-benzamidines were screened towards murine magnesium deficiency-dependent audiogenic seizures, unravelling two compounds with efficacious doses 50 (ED50) less than 10 mg/kg. They were also screened against maximal electroshock and subcutaneous pentylenetetrazole-induced seizures, and explored for superoxide -scavenging activity. 1,2-Ethane bis-1-amino-4-benzamidine (EBAB) was selected and evaluated in 6 Hz seizure test (ED50 = 49 mg/kg) and at 4 mu g/kg in focal cerebral ibotenate poisoning in pups (sizes of both white and grey matter wounds were halved). EBAB was further tested on NMDA-induced seizures in mice (ED50 = 6 mg/kg) and on H-3-TC-binding to a rodent cerebral preparation (IC50 = 1.4 mu M). Taken as a whole, present data emphasise the suitability of bis-benzamidines as templates for designing brain protective compounds. (c) 2010 Elsevier Masson SAS. All rights reserved.