3H-1,2,4-Triazol-3-one, 2,4-dihydro-4-methyl-5-(4-methylphenyl)- | 117258-23-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3H-1,2,4-Triazol-3-one, 2,4-dihydro-4-methyl-5-(4-methylphenyl)-
• 英文别名: 4-methyl-3-(4-methylphenyl)-1H-1,2,4-triazol-5-one
• CAS: 117258-23-8
• 化学式: C₁₀H₁₁N₃O
• 分子量: 189.217
• InChiKey: MEIWMIJMSLTVRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3H-1,2,4-Triazol-3-one, 2,4-dihydro-4-methyl-5-(4-methylphenyl)- 、 碘甲烷 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以56%的产率得到2,4-二甲基-5-(4-甲基苯基)-1,2,4-三唑-3-酮
  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
• 作为产物：
  描述：

  1-甲基-3-[(4-甲基苯甲酰)氨基]脲 在 sodium hydroxide 作用下， 反应 23.0h， 以78%的产率得到3H-1,2,4-Triazol-3-one, 2,4-dihydro-4-methyl-5-(4-methylphenyl)-
  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

• Substituted Arylimidazolone and Triazolone as Inhibitors of Vasopressin Receptors
  申请人：Meier Heinrich

  公开号：US20090312381A1

  公开（公告）日：2009-12-17

  The present application relates to novel, substituted 4-arylimidazol-2-ones and 5-aryl-1,2,4-triazolones, processes for the production thereof, the use thereof alone or in combinations for the treatment and/or prevention of diseases and the use thereof for the production of medicaments for the treatment and/or prevention of diseases, in particular for the treatment and/or prevention of cardiovascular diseases.

  本申请涉及新颖的取代的4-芳基咪唑-2-酮和5-芳基-1,2,4-三唑酮，其生产方法，单独或组合使用以治疗和/或预防疾病，以及用于生产治疗和/或预防疾病的药物，特别是用于治疗和/或预防心血管疾病。
• 3-Aryl-6-aryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles and related compounds as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cai Xiong Sui

  公开号：US20080113984A1

  公开（公告）日：2008-05-15

  Disclosed are 3-aryl-6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles and related compounds thereof, represented by the Formula I: wherein Ar 1 , Ar 2 , and X are defined herein. The present invention relates to the discovery that compounds having Formula I are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及公开的3-芳基-6-芳基-7H-[1,2,4]三唑并[3,4-b][1,3,4]噻二唑及其相关化合物，其由公式I表示：其中Ar1、Ar2和X在此定义。本发明涉及发现具有公式I的化合物是caspase激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于诱导在各种临床情况下发生异常细胞的无控制生长和扩散的细胞死亡。
• SUBSTITUTED ARYLIMIDAZOLONE AND TRIAZOLONE AS INHIBITORS OF VASOPRESSIN RECEPTORS
  申请人：Meier Heinrich

  公开号：US20130005704A1

  公开（公告）日：2013-01-03

  The present application relates to novel, substituted 4-arylimidazol-2-ones and 5-aryl-1,2,4-triazolones, processes for the production thereof, the use thereof alone or in combinations for the treatment and/or prevention of diseases and the use thereof for the production of medicaments for the treatment and/or prevention of diseases, in particular for the treatment and/or prevention of cardiovascular diseases.

  本申请涉及新型取代的4-芳基咪唑-2-酮和5-芳基-1,2,4-三唑酮，其生产过程，其单独或联合用于治疗和/或预防疾病的用途以及用于生产用于治疗和/或预防疾病的药物的用途，特别是用于治疗和/或预防心血管疾病。
• 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：——
• SUBSTITUIERTE ARYLIMIDAZ0L0NE UND -TRIAZ0L0NE ALS INHIBITOREN DER VASOPRESSIN-REZEPTOREN
  申请人：Bayer Pharma Aktiengesellschaft

  公开号：EP2027096B1

  公开（公告）日：2012-05-23