N-ethyl-2-[2-oxo-5-(pyridin-3-yl)-1,3-benzoxazol-3(2H)-yl]-N-phenylacetamide

• 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-ethyl-2-[2-oxo-5-(pyridin-3-yl)-1,3-benzoxazol-3(2H)-yl]-N-phenylacetamide
• 英文别名: N-ethyl-2-(2-oxo-5-pyridin-3-yl-1,3-benzoxazol-3-yl)-N-phenylacetamide
• 化学式: C₂₂H₁₉N₃O₃
• 分子量: 373.411
• InChiKey: AWITUAPEDVIANH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 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：
  62.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [2-oxo-5-(pyridin-3-yl)-1,3-benzoxazol-3(2H)-yl]acetic acid hydrochloride 、 N-乙基苯胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以28%的产率得到N-ethyl-2-[2-oxo-5-(pyridin-3-yl)-1,3-benzoxazol-3(2H)-yl]-N-phenylacetamide
  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

文献信息

• Identification of a Novel Benzoxazolone Derivative as a Selective, Orally Active 18 kDa Translocator Protein (TSPO) Ligand
  作者：Takayuki Fukaya、Takeo Ishiyama、Satoko Baba、Shuji Masumoto

  DOI：10.1021/jm401325r

  日期：2013.10.24

  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.