2-[(E)-[1-(4-methoxyphenyl)-2-phenylethylidene]amino]guanidine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-[(E)-[1-(4-methoxyphenyl)-2-phenylethylidene]amino]guanidine
• 化学式: C₁₆H₁₈N₄O
• 分子量: 282.345
• InChiKey: HRAYSXVLVYXOSV-XDJHFCHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 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：
  86
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-甲氧基-2-苯基苯乙酮 、 氨基胍媒染剂 在 盐酸 作用下， 以 水 、 异丙醇 为溶剂， 反应 24.0h， 以57%的产率得到2-[(E)-[1-(4-methoxyphenyl)-2-phenylethylidene]amino]guanidine
  参考文献：
  名称：

  Synthesis and antiseizure activity of (E)-1,2-diarylethylidenehydrazine carboximidamides against tonic-clonic seizures: an intracerebroventricular and electrophysiological study

  摘要：

  A series of (E)-1,2-diarylethylidenehydrazine carboximidamides2a-jwere synthesized and characterized by NOESY experiment as anticonvulsant agents and their antiseizure activity was evaluated by intracerebroventricular administration of compounds. Most of the compounds had significant protection against tonic-clonic seizures and2awas found to be as equipotent as carbamazepine in seizures control. In order to find their anticonvulsant mechanism of action,2awas subjected to further electrophysiological studies using patch-clamp technique. The results confirmed that this compound is neither a voltage-gated sodium channel blocker nor a NMDA/AMPA antagonist. Although2adid not show any direct GABA agonistic activity, it could decrease EPSP and increase IPSP frequency without any change in amplitude. Finally, the results indicated most likely a presynaptic GABA-mediated mechanism of2afor its antiseizure activity such as inhibition of the GABA-T which was validated by molecular docking.

  DOI：

  10.1007/s00044-020-02576-7

文献信息

• Synthesis and antiseizure activity of (E)-1,2-diarylethylidenehydrazine carboximidamides against tonic-clonic seizures: an intracerebroventricular and electrophysiological study
  作者：Fariba Abedi Firouzjaei、Elmira Heidarli、Shabnam Ravan、Sayed Masoud Hosseini、Nima Naderi、Kiarash Almasyan、Afshin Sarvary、Hamid Irannejad

  DOI：10.1007/s00044-020-02576-7

  日期：2020.8

  A series of (E)-1,2-diarylethylidenehydrazine carboximidamides2a-jwere synthesized and characterized by NOESY experiment as anticonvulsant agents and their antiseizure activity was evaluated by intracerebroventricular administration of compounds. Most of the compounds had significant protection against tonic-clonic seizures and2awas found to be as equipotent as carbamazepine in seizures control. In order to find their anticonvulsant mechanism of action,2awas subjected to further electrophysiological studies using patch-clamp technique. The results confirmed that this compound is neither a voltage-gated sodium channel blocker nor a NMDA/AMPA antagonist. Although2adid not show any direct GABA agonistic activity, it could decrease EPSP and increase IPSP frequency without any change in amplitude. Finally, the results indicated most likely a presynaptic GABA-mediated mechanism of2afor its antiseizure activity such as inhibition of the GABA-T which was validated by molecular docking.