2-[2-(4-Chloro-phenyl)-benzoimidazol-1-yl]-N,N-dipropyl-acetamide | 135429-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-[2-(4-Chloro-phenyl)-benzoimidazol-1-yl]-N,N-dipropyl-acetamide
• 英文别名: 2-[2-(4-chlorophenyl)benzimidazol-1-yl]-N,N-dipropylacetamide
• CAS: 135429-04-8
• 化学式: C₂₁H₂₄ClN₃O
• 分子量: 369.894
• InChiKey: HIFNVXDJGHXJRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  [2-(4-Chloro-phenyl)-benzoimidazol-1-yl]-acetic acid 、 二正丙胺 在 N,N'-羰基二咪唑 作用下， 生成 2-[2-(4-Chloro-phenyl)-benzoimidazol-1-yl]-N,N-dipropyl-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