2-[2-[4-(Trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-3-yl]acetamide | 135428-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[2-[4-(Trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-3-yl]acetamide
• CAS: 135428-91-0
• 化学式: C₁₅H₁₁F₃N₄O
• 分子量: 320.274
• InChiKey: WWQKAOKBUZCUNK-UHFFFAOYSA-N

物化性质

• 沸点：
  519.9±60.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  73.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(3-amino-2-pyridinyl)glycine ethyl ester 在 sodium hydroxide 、 氯化亚砜 、 氨 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.21h， 生成 2-[2-[4-(Trifluoromethyl)phenyl]imidazo[4,5-b]pyridin-3-yl]acetamide
  参考文献：
  名称：

  2-Phenyl-3H-imidazo[4,5-b]pyridine-3-acetamides as nonbenzodiazepine anticonvulsants and anxiolytics

  摘要：

  A series of 2-phenyl-3H-imidazo[4,5-b]pyridine-3-acetamides were designed and synthesized as non-benzodiazepine anxiolytics based on a molecular disconnection of a typical 1,4-benzodiazepine (BZD). A number of these compounds showed submicromolar potency in a [H-3]benzodiazepine binding assay in vitro and good potency in protecting rodents against pentylenetetrazole-induced seizures. Compound 84 appears to be a selective anticonvulsant (pentylenetetrazole) agent when tested against a profile of chemically and electrically induced seizures in mice. In addition, compound 148 appears to be a selective anxiolytic/hypnotic agent on the basis of biochemical and pharmacological characterization. It appears to be a full BZD agonist as assessed by GABA shift ratio and to be effective in punishment and nonpunishment animal models of anxiety. In addition, it shows a lower side-effect profile than diazepam as assessed by rotorod neurotoxicity and potentiation of ethanol-induced sleep time in mice. The chemistry and structure-activity relationships of this series is discussed.

  DOI：

  10.1021/jm00114a007