4-(4-hydroxybenzylidene)amino-3,5-dimethylpyrazole | 1228345-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(4-hydroxybenzylidene)amino-3,5-dimethylpyrazole
• 英文别名: 4-[(3,5-dimethyl-1H-pyrazol-4-yl)iminomethyl]phenol
• CAS: 1228345-58-1
• 化学式: C₁₂H₁₃N₃O
• 分子量: 215.255
• InChiKey: FBLTXTSIDOTVQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,5-二甲基-1H-吡唑-4-胺 、 水杨醛 以 甲醇 为溶剂， 反应 0.5h， 以56%的产率得到4-(4-hydroxybenzylidene)amino-3,5-dimethylpyrazole
  参考文献：
  名称：

  Anticonvulsant activity of 3,5-dimethylpyrazole derivatives in animal models

  摘要：

  A series of 3,5-dimethylpyrazole derivatives, structurally related to the previously described potent ameltolide analogues, were synthesized and evaluated for their anticonvulsant activity. Ten compounds were prepared by reacting the 4-amino-3,5-dimethylpyrazole with appropriate substituted carboxylic acids, benzoyl chlorides and benzaldehydes to obtain amide and imine derivatives. Initial anticonvulsant screening was performed using intraperitoneal pentylenetetrazole (PTZ) and maximal electroshock (MES) induced seizure tests in mice. Among the 10 tested compounds, N-[1-(4-methoxybenzoyl)-3,5-dimethylpyrazole-4-yl]-4-methoxybenzamide 2 and N-[1-(2,6-dichlorobenzoyl)-3,5-dimethylpyrazole-4-yl]-2,6-dichlorobenzamide 3 decreased seizure severity and the mortality rate in the PTZ test. Hence, compound 3 was tested in an animal model of absence epilepsy, Genetic Absence Epileptic Rats from Strasbourg (GAERS). There were no significant changes in the duration or number of spike-and-wave discharges in this model.

  DOI：

  10.1007/s00044-010-9358-6