5-(4-Chlorophenyl)-2,4-dihydro-4-ethyl-2-methyl-3H-1,2,4-triazol-3-one | 116114-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-Chlorophenyl)-2,4-dihydro-4-ethyl-2-methyl-3H-1,2,4-triazol-3-one
• 英文别名: 5-(4-Chlorophenyl)-4-ethyl-2-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one；2,4-Dihydro-5-(4-chlorophenyl)-4-ethyl-2-methyl-3H-1,2,4-triazol-3-one；5-(4-chlorophenyl)-4-ethyl-2-methyl-1,2,4-triazol-3-one
• CAS: 116114-14-8
• 化学式: C₁₁H₁₂ClN₃O
• 分子量: 237.689
• InChiKey: HXPJLBHKHCQJBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  35.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-Chlorophenyl)-2,4-dihydro-4-ethyl-2-methyl-3H-1,2,4-triazol-3-one 在 双(三环己基锡(IV))硫醚 、 三氯化硼 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 17.0h， 以73%的产率得到5-(4-氯苯基)-4-乙基-2-甲基-1,2,4-三唑-3-硫酮
  参考文献：
  名称：

  The Bis(tricyclohexylstannyl) Sulfide Thionation of 3H-1,2,4- Triazol-3-ones

  摘要：

  使用双(三环己基锡)硫醚/三氯化硼组合，5-芳基-2,4-二烷基-2,4-二氢-3H-1,2,4-三唑-3-酮可以以55-74%的产率转化为相应的3H-1,2,4-三唑-3-硫酮。

  DOI：

  10.1055/s-1987-28119
• 作为产物：
  描述：

  4-氯苯甲酰肼 在 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 64.0h， 生成 5-(4-Chlorophenyl)-2,4-dihydro-4-ethyl-2-methyl-3H-1,2,4-triazol-3-one
  参考文献：
  名称：

  2,4-Dihydro-3H-1,2,4-triazol-3-ones as anticonvulsant agents

  摘要：

  A series of 5-aryl-2,4-dihydro-3H-1,2,4-triazol-3-ones was evaluated for anticonvulsant activity. In general the members of this series were prepared by the alkaline cyclization of 1-aroyl-4-alkylsemicarbazides. The resulting 2-unsubstituted 3H-1,2,4-triazol-3-ones were then alkylated, yielding 2,4-dialkyl-3H-1,2,4-triazol-3-ones. Approximately one-third of the compounds examined exhibited activity against both maximal electroshock- and pentylenetetrazole-induced seizures in mice. Receptor-binding studies suggest that this activity was not a consequence of activity at either benzodiazepine or NMDA-type glutamate receptors. From this series, compound 45 was selected for further evaluation where it was also found to be active against 3-mercaptopropionic acid, bicuculline, and quinolinic acid induced seizures in mice. In addition, 45 also protected gerbils from hippocampal neuronal degeneration produced by either hypoxia or intrastriatal quinolinic acid injection.

  DOI：

  10.1021/jm00172a015

文献信息

• Process for the preparation of 5-aryl-2,4-dialkyl-3H-1,2,4-triazole-3-thiones
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0280867A1

  公开（公告）日：1988-09-07

  This invention relates to a novel process for the preparation of 5-aryl-2,4-dialkyl-3H-1,2,4-triazole-3-­thiones, useful as antidepressants, through the thionation of the corresponding 5-aryl-2,4-dialkyl-3H-1,2,4-triazol-­3-ones.

  这项发明涉及一种新型制备5-芳基-2,4-二烷基-3H-1,2,4-三唑-3-硫酮的过程，该化合物可用作抗抑郁药，通过将相应的5-芳基-2,4-二烷基-3H-1,2,4-三唑-3-酮进行硫化来实现。
• 5-aryl-3H-1,2,4-triazol-3-ones and their use in the treatment of
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05436252A1

  公开（公告）日：1995-07-25

  This invention relates to neuroprotective 5-aryl-3H-1,2,4-triazol-3-ones and to their use in the treatment of neurodegenerative disorders such as cerebral ischemia, stroke, Alzheimer's disease, Parkinson's disease, and Huntington's disease.

  本发明涉及神经保护性5-芳基-3H-1,2,4-三唑-3-酮及其在治疗神经退行性疾病如脑缺血、中风、阿尔茨海默病、帕金森病和亨廷顿病中的应用。
• 5-phenyl-3H-1,2,4-triazol-3-ones and their use as anticonvulsants
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US04946856A1

  公开（公告）日：1990-08-07

  This invention relates to 5-phenyl-3H-1,2,4-triazol-3-ones and to their use as anticonvulsants for treatment of seizure disorders.

  这项发明涉及5-苯基-3H-1,2,4-三唑-3-酮及其作为抗癫痫药物治疗癫痫症的用途。
• KANE, JOHN M.;BARON, BRUCE M.;DUDLEY, MARK W.;SORENSEN, STEPHEN M.;STAEGE+, J. MED. CHEM., 33,(1990) N0, C. 2772-2777
  作者：KANE, JOHN M.、BARON, BRUCE M.、DUDLEY, MARK W.、SORENSEN, STEPHEN M.、STAEGE+

  DOI：——

  日期：——
• KANE, JOHN M., SYNTHESIS,(1987) N 10, 912-914
  作者：KANE, JOHN M.

  DOI：——

  日期：——