N-methyl-2-{2-oxo-5-[4-(trifluoromethoxy)phenyl]-1,3-benzoxazol-3(2H)-yl}-N-(pyridin-3-yl)acetamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: N-methyl-2-{2-oxo-5-[4-(trifluoromethoxy)phenyl]-1,3-benzoxazol-3(2H)-yl}-N-(pyridin-3-yl)acetamide
• 英文别名: N-Methyl-N-(3-pyridyl)-5-[p-(trifluoromethoxy)phenyl]-2-oxo-2,3-dihydrobenzoxazole-3-acetamide；N-methyl-2-[2-oxo-5-[4-(trifluoromethoxy)phenyl]-1,3-benzoxazol-3-yl]-N-pyridin-3-ylacetamide
• 化学式: C₂₂H₁₆F₃N₃O₄
• 分子量: 443.382
• InChiKey: GMKINZFNPNPKFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-methyl-2-{2-oxo-5-[4-(trifluoromethoxy)phenyl]-1,3-benzoxazol-3(2H)-yl}-N-(pyridin-3-yl)acetamide 在 盐酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 0.5h， 以88%的产率得到N-methyl-2-{2-oxo-5-[4-(trifluoromethoxy)phenyl]-1,3-benzoxazol-3(2H)-yl}-N-(pyridin-3-yl)acetamide hydrochloride
  参考文献：
  名称：

  Identification of a Novel Benzoxazolone Derivative as a Selective, Orally Active 18 kDa Translocator Protein (TSPO) Ligand

  摘要：

  Optimization of the pharmacokinetic properties for a series of benzoxazolone derivatives led to the identification of 9b, which showed anxiolytic effect in a rat model. However, 9b, like known benzodiazepines, induced motor impairment. Investigation into the cause of this unexpected side effect and management of 9b off-target binding affinity led to the identification of 10d, which showed oral anxiolytic effect in the rat model with improved safety profile.

  DOI：

  10.1021/jm401325r
• 作为产物：
  描述：

  4-溴-2-硝基苯酚 在 盐酸 、 四(三苯基膦)钯 、 rhodium contaminated with carbon 、 氢气 、 potassium carbonate 、 1-羟基苯并三唑 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.0h， 生成 N-methyl-2-{2-oxo-5-[4-(trifluoromethoxy)phenyl]-1,3-benzoxazol-3(2H)-yl}-N-(pyridin-3-yl)acetamide
  参考文献：
  名称：

  Identification of a Novel Benzoxazolone Derivative as a Selective, Orally Active 18 kDa Translocator Protein (TSPO) Ligand

  摘要：

  Optimization of the pharmacokinetic properties for a series of benzoxazolone derivatives led to the identification of 9b, which showed anxiolytic effect in a rat model. However, 9b, like known benzodiazepines, induced motor impairment. Investigation into the cause of this unexpected side effect and management of 9b off-target binding affinity led to the identification of 10d, which showed oral anxiolytic effect in the rat model with improved safety profile.

  DOI：

  10.1021/jm401325r