8-(6-methoxy-4-methylpyridin-3-yl)-2,7-dimethyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one | 1149605-56-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 8-(6-methoxy-4-methylpyridin-3-yl)-2,7-dimethyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one
• CAS: 1149605-56-0
• 化学式: C₁₄H₁₅N₅O₂
• 分子量: 285.305
• InChiKey: VZOORRSLBLUTTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  81.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  8-(6-methoxy-4-methylpyridin-3-yl)-2,7-dimethyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one 在 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 4-Chloro-8-(6-methoxy-4-methylpyridin-3-yl)-2,7-dimethylpyrazolo[1,5-a][1,3,5]triazine
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 8-(Pyrid-3-yl)pyrazolo[1,5-a]-1,3,5-triazines: Potent, Orally Bioavailable Corticotropin Releasing Factor Receptor-1 (CRF₁) Antagonists

  摘要：

  This report describes the syntheses and structure-activity relationships of 8-(substituted pyridyl)pyrazolo[1,5-a]-1,3,5-triazine corticotropin releasing factor receptor-1 (CRF1) receptor antagonists. These CRF1 receptor antagonists may be potential anxiolytic or antidepressant drugs. This research resulted in the discovery of compound 13-15, which is a potent, selective CRF1 antagonist (hCRF(1) IC50 = 6.1 +/- 0.6 nM) with weak affinity for the CRF-binding protein and biogenic amine receptors. This compound also has a good pharmacokinetic profile in dogs. Analogue 13-15 is orally effective in two rat models of anxiety: the defensive withdrawal (situational anxiety) model and the elevated plus maze test. Analogue 13-15 has been advanced to clinical trials.

  DOI：

  10.1021/jm900025h
• 作为产物：
  描述：

  C₂H₄O₂*C₁₃H₁₇N₅O 、 碳酸二乙酯 在 乙醇 、 sodium 作用下， 反应 18.0h， 生成 8-(6-methoxy-4-methylpyridin-3-yl)-2,7-dimethyl-3H-pyrazolo[1,5-a][1,3,5]triazin-4-one
  参考文献：
  名称：

  Synthesis and Structure−Activity Relationships of 8-(Pyrid-3-yl)pyrazolo[1,5-a]-1,3,5-triazines: Potent, Orally Bioavailable Corticotropin Releasing Factor Receptor-1 (CRF₁) Antagonists

  摘要：

  This report describes the syntheses and structure-activity relationships of 8-(substituted pyridyl)pyrazolo[1,5-a]-1,3,5-triazine corticotropin releasing factor receptor-1 (CRF1) receptor antagonists. These CRF1 receptor antagonists may be potential anxiolytic or antidepressant drugs. This research resulted in the discovery of compound 13-15, which is a potent, selective CRF1 antagonist (hCRF(1) IC50 = 6.1 +/- 0.6 nM) with weak affinity for the CRF-binding protein and biogenic amine receptors. This compound also has a good pharmacokinetic profile in dogs. Analogue 13-15 is orally effective in two rat models of anxiety: the defensive withdrawal (situational anxiety) model and the elevated plus maze test. Analogue 13-15 has been advanced to clinical trials.

  DOI：

  10.1021/jm900025h