(5-methoxy-2-phenylindol-3-yl)glyoxylyl chloride | 1060749-15-6

• 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: (5-methoxy-2-phenylindol-3-yl)glyoxylyl chloride
• CAS: 1060749-15-6
• 化学式: C₁₇H₁₂ClNO₃
• 分子量: 313.74
• InChiKey: CCHDLLMAXTTYSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.79
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  59.16
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  二已胺 、 (5-methoxy-2-phenylindol-3-yl)glyoxylyl chloride 在 三乙胺 作用下， 以 甲苯 为溶剂， 以38%的产率得到N,N-dihexyl-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
• 作为产物：
  描述：

  草酰氯 、 5-甲氧基-2-苯基-1H-吲哚 以 乙醚 为溶剂， 以98%的产率得到(5-methoxy-2-phenylindol-3-yl)glyoxylyl chloride
  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