5-(thien-2-yl)-2,4-dihydro-4-methyl-3H-1,2,4-triazol-3-one | 117258-29-4

• 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-(thien-2-yl)-2,4-dihydro-4-methyl-3H-1,2,4-triazol-3-one
• 英文别名: 5-(2-thienyl)-2,4-dihydro-4-methyl-3H-1,2,4-triazol-3-one；3H-1,2,4-Triazol-3-one, 2,4-dihydro-4-methyl-5-(2-thienyl)-；4-methyl-3-thiophen-2-yl-1H-1,2,4-triazol-5-one
• CAS: 117258-29-4
• 化学式: C₇H₇N₃OS
• 分子量: 181.218
• InChiKey: RGXRZHGPTUWEOH-UHFFFAOYSA-N

物化性质

• 熔点：
  183-185 °C(Solv: isopropanol (67-63-0))
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(thien-2-yl)-2,4-dihydro-4-methyl-3H-1,2,4-triazol-3-one 、 碘乙烷 生成 5-(thien-2-yl)-2,4-dihydro-2-ethyl-4-methyl-3H-1,2,4-triazol-3-one
  参考文献：
  名称：

  KANE, JOHN M.;BARON, BRUCE M.;DUDLEY, MARK W.;SORENSEN, STEPHEN M.;STAEGE+, J. MED. CHEM., 33,(1990) N0, C. 2772-2777

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-Thienoyl)-4-methylsemicarbazide 在 sodium hydroxide 作用下， 反应 23.0h， 以82%的产率得到5-(thien-2-yl)-2,4-dihydro-4-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

• 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.

  这项发明涉及神经保护性的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-Aryl-3H-1,2,4-triazol-3-ones and their use in the treatment of neurodegenerative disorders
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0273309B1

  公开（公告）日：1995-01-11
• US5436252A
  申请人：——

  公开号：US5436252A

  公开（公告）日：1995-07-25