N-(1-naphthyl)-N'-(m-ethylphenyl)-N'-ethylguanidine | 137159-93-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(1-naphthyl)-N'-(m-ethylphenyl)-N'-ethylguanidine
• 英文别名: CNS 1103；N-ethyl-N-(m-ethylphenyl)-N'-(1-naphthyl)guanidine；N-ethyl-N-(m-ethylphenyl)-N'-(1naphthyl)guanidine；1-ethyl-1-(3-ethylphenyl)-2-naphthalen-1-ylguanidine
• CAS: 137159-93-4
• 化学式: C₂₁H₂₃N₃
• 分子量: 317.434
• InChiKey: SRNKBLLOXBRIAX-UHFFFAOYSA-N

物化性质

• 沸点：
  466.9±38.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-萘胺盐酸盐 、 N-(m-ethylphenyl)-N-ethylcyanamide 以18%的产率得到N-(1-naphthyl)-N'-(m-ethylphenyl)-N'-ethylguanidine
  参考文献：
  名称：

  N，N′-二芳基胍衍生物的合成和结构活性研究。N-（1-萘基）-N'-（3-乙基苯基）-N'-甲基胍：一种新的选择性非竞争性NMDA受体拮抗剂。

  摘要：

  作为NMDA受体离子通道位点配体的二芳基胍代表了一类潜在的神经保护药物。合成了与N，N'-二邻甲苯基胍（DTG）（一种已知的选择性sigma受体配体）结构相关的几种二芳基胍，并使用NMDA受体在大鼠或豚鼠脑膜匀浆中进行了体外放射性配体置换试验，并进行了评估。离子通道位点特异性放射性配体[3H]-（+）-5（S）-甲基-10（R），11-二氢-5H-二苯并[a，d]环庚烯-5，10-亚胺（MK-801，3 ），以及sigma受体特异性放射性配体[3H]-二邻甲苯基胍（DTG，5）。本文介绍了导致新的三和四取代的胍的结构-活性关系，其对NMDA受体离子通道位点具有高选择性，对sigma受体的亲和力弱或微不足道。对称取代的二苯基胍的体外结合结果表明，在苯环上具有邻或间取代基（相对于胍氮的位置）的化合物与对位取代的衍生物相比，对NMDA受体离子通道位点的亲和力更高。在针对对称二芳基胍研究的一组环取

  DOI：

  10.1021/jm00028a009

文献信息

• Tri- and tetra-substituted guanidines and their use as excitatory amino
  申请人：State of Oregon, acting by and through the Oregon State Board of Higher

  公开号：US05637622A1

  公开（公告）日：1997-06-10

  Tri- and tetra-substituted guanidines which exhibit a high binding affinity to phencyclidine (PCP) receptors and, more preferably, low affinity to the brain sigma receptors. These guanidine derivatives act as non-competitive inhibitors of glutamate induced responses of the NMDA receptor by acting as blockers for the ion channel of the NMDA receptor-ion channel complex. These compounds thus exert neuroprotective activity and are useful in the therapeutic treatment of neuronal loss in hypoxia, hypoglycemia, brain or spinal cord ischemia, and brain or spinal chord trauma as well as being useful for the treatment of epilepsy, Alzheimer's disease, Amyotrophic Lateral Sclerosis, Parkinson's disease, Huntington's disease, Down's Syndrome, Korsakoff's disease and other neurodegenerative disorders.

  三取代和四取代的胍基化合物具有高结合亲和力，可与苯环环庚啡（PCP）受体结合，更好的是，它们对大脑σ受体的亲和力较低。这些胍基衍生物作为非竞争性抑制剂，通过作为NMDA受体离子通道复合物的通道阻滞剂，阻止谷氨酸诱导的NMDA受体反应。这些化合物因此具有神经保护活性，并可用于治疗低氧、低血糖、脑或脊髓缺血、脑或脊髓创伤引起的神经元丧失，并且对于治疗癫痫、阿尔茨海默病、肌萎缩性侧索硬化、帕金森病、亨廷顿病、唐氏综合症、科萨科夫病和其他神经退行性疾病也有用。
• Tri-and tetra-substituted guanidines and their use as excitatory amino
  申请人：State of Oregon, acting by and through the Oregon State Board of Higher

  公开号：US05767162A1

  公开（公告）日：1998-06-16

  Tri- and tetra-substituted guanidines which exhibit a high binding affinity to phencyclidine (PCP) receptors and, more preferably, low affinity to the brain sigma receptors. These guanidine derivatives act as non-competitive inhibitors of glutamate induced responses of the NMDA receptor by acting as blockers for the ion channel of the NMDA receptor-ion channel complex. These compounds thus exert neuroprotective activity and are useful in the therapeutic treatment of neuronal loss in hypoxia, hypoglycemia, brain or spinal cord ischemia, and brain or spinal chord trauma as well as being useful for the treatment of epilepsy, Alzheimer's disease, Amyotrophic Lateral Sclerosis, Parkinson's disease, Huntington's disease, Down's Syndrome, Korsakoff's disease and other neurodegenerative disorders.

  三取代和四取代的胍基化合物具有高结合亲和力，可与苯环哌啶（PCP）受体结合，并更倾向于低亲和力与大脑西格玛受体结合。这些胍基衍生物作为非竞争性抑制剂，通过阻断NMDA受体离子通道复合物的离子通道作用，从而抑制谷氨酸诱导的NMDA受体反应。这些化合物因此具有神经保护作用，并可用于治疗缺氧、低血糖、脑或脊髓缺血、脑或脊髓创伤以及癫痫、阿尔茨海默病、肌萎缩性侧索硬化、帕金森病、亨廷顿病、唐氏综合症、科萨科夫病和其他神经退行性疾病的治疗。
• Tri-and tetra-substituted guanidines and their use as excitatory amino acid antagonists
  申请人：State of Oregon, acting by and through the Oregon State Board of Higher Education, acting for and on behalf of the Oregon Health Sciences University and the University of Oregon

  公开号：US06251948B1

  公开（公告）日：2001-06-26

  Tri- and tetra-substituted guanidines which exhibit a high binding affinity to phencyclidine (PCP) receptors and, more preferably, low affinity to the brain sigma receptors. These guanidine derivatives act as non-competitive inhibitors of glutamate induced responses of the NMDA receptor by acting as blockers for the ion channel of the NMDA receptor-ion channel complex. These compounds thus exert neuroprotective activity and are useful in the therapeutic treatment of neuronal loss in hypoxia, hypoglycemia, brain or spinal cord ischemia, and brain or spinal chord trauma as well as being useful for the treatment of epilepsy, Alzheimer's disease, Amyotrophic Lateral Sclerosis, Parkinson's disease, Huntington's disease, Down's Syndrome, Korsakoff's disease and other neurodegenerative disorders.

  三取代和四取代的胍基化合物具有高结合亲和力，可以结合到苯环环庚啡（PCP）受体，更好的是，这些化合物对大脑σ受体的亲和力较低。这些胍基衍生物作为非竞争性抑制剂，通过作为NMDA受体离子通道复合物的通道阻滞剂，来抑制谷氨酸诱导的NMDA受体响应。因此，这些化合物具有神经保护作用，并可用于治疗缺氧、低血糖、脑或脊髓缺血、脑或脊髓创伤以及癫痫、阿尔茨海默病、肌萎缩性侧索硬化症、帕金森病、亨廷顿病、唐氏综合症、科萨科夫氏综合症和其他神经退行性疾病的治疗。
• Methods of treatment of eye trauma and disorders
  申请人：——

  公开号：US20030027801A1

  公开（公告）日：2003-02-06

  Methods are provided for treatment of eye disorders and injury, including methods for treatment of reduced flow of blood or other nutrients to retinal tissue and/or optic nerve, methods for treatment of retinal ischemia and trauma and methods for treatment for optic nerve injury/damage.

  提供了治疗眼部疾病和损伤的方法，包括治疗流向视网膜组织和/或视神经的血液或其他营养物质减少的方法、治疗视网膜缺血和创伤的方法以及治疗视神经损伤/损坏的方法。
• EP0517852A4
  申请人：——

  公开号：EP0517852A4

  公开（公告）日：1994-03-02