N,N-dibutyl-2-(5-methoxy-2-phenyl-1H-indol-3-yl)-2-oxoacetamide | 1060748-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N,N-dibutyl-2-(5-methoxy-2-phenyl-1H-indol-3-yl)-2-oxoacetamide
• CAS: 1060748-47-1
• 化学式: C₂₅H₃₀N₂O₃
• 分子量: 406.525
• InChiKey: BBDRAMJWBYOEQX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (5-methoxy-2-phenylindol-3-yl)glyoxylyl chloride 、 二正丁胺 在 三乙胺 作用下， 以 甲苯 为溶剂， 以59%的产率得到N,N-dibutyl-2-(5-methoxy-2-phenyl-1H-indol-3-yl)-2-oxoacetamide
  参考文献：
  名称：

  Anxiolytic-like Effects of N,N-Dialkyl-2-phenylindol-3-ylglyoxylamides by Modulation of Translocator Protein Promoting Neurosteroid Biosynthesis

  摘要：

  Novel N,N-disubstituted indol-3-ylglyoxylamides (1-56), bearing different combinations of substituents R-1-R-5, were synthesized and evaluated as ligands of the translocator protein (TSPO), the 18 kDa protein representing the minimal functional unit of the "peripheral-type benzodiazepine receptor" (PBR). Most of the new compounds showed a nanomolar/subnanomolar affinity for TSPO and stimulated steroid biosynthesis in rat C6 glioma cells with a potency similar to or higher than that of classic TSPO ligands such as PK 11195. Moreover, when evaluated in vivo by means of the elevated-plus-maze (EPM) paradigm in the rat, compound 32. the best-performing derivative in terms of TSPO affinity and pregnenolone production, showed clear anxiolytic effects. The results of this study suggested that the novel N, N-di substituted indol-3y1glyoxylani ides may represent a promising class of compounds potentially suited for the treatment of anxiety disorders.

  DOI：

  10.1021/jm8003224