N,N'-bis(4-cyanophenyl)ethylenediamine | 101351-75-1

• 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,N'-bis(4-cyanophenyl)ethylenediamine
• 英文别名: 1.2-Bis-<4-cyan-anilino>-ethan；4,4'-(1,2-ethanediyldiimino)bis-(benzonitrile)；4-[2-(4-Cyanoanilino)ethylamino]benzonitrile
• CAS: 101351-75-1
• 化学式: C₁₆H₁₄N₄
• 分子量: 262.314
• InChiKey: ZNQWULDGVCIJKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  71.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  对氟苯腈 、 乙二胺 在 potassium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以64%的产率得到N,N'-bis(4-cyanophenyl)ethylenediamine
  参考文献：
  名称：

  合成获得DNA和RNA 5'-醛类病变的化学多样性

  摘要：

  从DNA中核苷酸的C5'位置提取氢原子会导致直接的分裂，原因是从被氧化的核苷酸生成对碱不稳定的片段。主要损害在于含有5'-醛的末端，该5'-醛是原本未损坏的核苷酸的一部分。而且，由于它可以被DNA中遇到的四个核苷中的任何一个携带，因此被认为是多态性DNA链断裂损伤。在这里，我们建议快速合成以该5'-醛基（5'-AODN）结尾的寡核苷酸（ON）。这种简单而廉价的策略依赖于在固体支持物上进行的Pfitzner-Moffatt氧化，然后是对所得醛功能的瞬时保护。该方法与5'-末端核碱基无关，最有趣的是可以直接扩展至RNA以产生相应的5'-AORN。

  DOI：

  10.1021/jo502170e

文献信息

• 1,4–Diarylpiperazines and analogs as anti-tubercular agents: Synthesis and biological evaluation
  作者：D. Forge、D. Cappoen、J. Laurent、D. Stanicki、A. Mayence、T.L. Huang、L. Verschaeve、K. Huygen、J.J. Vanden Eynde

  DOI：10.1016/j.ejmech.2011.12.035

  日期：2012.3

  bacillary persistence and human immunodeficiency virus (HIV) co-infection hamper current drug treatment to completely cure the infection, generating a constant demand for novel drug candidates to tackle these problems. A small library of novel heterocyclic compounds was screened in a rapid luminometric in vitro assay against the laboratory M.tb. strain H37Rv. A group of amidines was found to have the highest

  尽管现代化学疗法在抗击结核病方面取得了进展，但致病菌结核分枝杆菌（M.tb.）仍未根除。细菌对抗分枝杆菌药的耐药性，细菌持续性和人类免疫缺陷病毒（HIV）共同感染阻碍了目前的药物治疗以完全治愈感染，从而产生了不断寻求新的候选药物来解决这些问题的需求。 在针对实验室M.tb的快速光度体外测定中筛选了一个小的新型杂环化合物文库。H37Rv株。发现一组of具有最高的效力，并进一步评估了其对C3A肝细胞的急性毒性。接下来，评估了最有前途的化合物对多药耐药临床分离株的活性。还测试了idine的组杀死细胞内M.tb的能力。驻留在小鼠J774A.1巨噬细胞中。最后，我们报告了化合物的结构差异与其抗分枝杆菌活性之间的相关性。
• LOWN J. W.; SINGH R., CAN. J. CHEM., 1981, 59, NO 9, 1347-1356
  作者：LOWN J. W.、 SINGH R.

  DOI：——

  日期：——
• 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.
• Synthetic Access to the Chemical Diversity of DNA and RNA 5′-Aldehyde Lesions
  作者：Rémy Lartia、Jean-François Constant

  DOI：10.1021/jo502170e

  日期：2015.1.16

  C5′-position of nucleotides in DNA results in direct strand scission by generating alkali-labile fragments from the oxidized nucleotide. The major damage consists in a terminus containing a 5′-aldehyde as part of an otherwise undamaged nucleotide. Moreover it is considered as a polymorphic DNA strand break lesion since it can be borne by any of the four nucleosides encountered in DNA. Here we propose an expeditious

  从DNA中核苷酸的C5'位置提取氢原子会导致直接的分裂，原因是从被氧化的核苷酸生成对碱不稳定的片段。主要损害在于含有5'-醛的末端，该5'-醛是原本未损坏的核苷酸的一部分。而且，由于它可以被DNA中遇到的四个核苷中的任何一个携带，因此被认为是多态性DNA链断裂损伤。在这里，我们建议快速合成以该5'-醛基（5'-AODN）结尾的寡核苷酸（ON）。这种简单而廉价的策略依赖于在固体支持物上进行的Pfitzner-Moffatt氧化，然后是对所得醛功能的瞬时保护。该方法与5'-末端核碱基无关，最有趣的是可以直接扩展至RNA以产生相应的5'-AORN。