ethyl 4-bromo-3-methoxyindole-2-carboxylate | 153501-23-6

• 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: ethyl 4-bromo-3-methoxyindole-2-carboxylate
• 英文别名: ethyl 4-bromo-3-methoxy-1H-indole-2-carboxylate
• CAS: 153501-23-6
• 化学式: C₁₂H₁₂BrNO₃
• 分子量: 298.136
• InChiKey: IYYXHKWEDFWHKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-bromo-3-methoxyindole-2-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以86%的产率得到4-bromo-3-methoxyindole-2-carboxylic acid
  参考文献：
  名称：

  Synthesis, pharmacology and therapeutic potential of 10-methoxypyrazino[1,2-a]indoles, partial agonists at the 5HT2C receptor

  摘要：

  A series of new 10-methoxypyrazino[1,2-a]indoles has been prepared and shown to be 5HT(2C) receptor ligands. The studied compounds 10a-j were found to act as partial agonists at the 5HT(2C) receptor, binding with high affinity and moderate selectivity versus 5HT(1A) and 5HT(2A) receptors, but inducing only a submaximal increase in phosphoinositol formation. Compound 10j was demonstrated to be active in animal models of obsessive-compulsive disorder, depression and panic anxiety.

  DOI：

  10.1016/s0223-5234(97)83976-1
• 作为产物：
  描述：

  ethyl N-[3-bromo-2-(ethoxycarbonyl)phenyl]glycinate 在 sodium 作用下， 以 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 2.5h， 生成 ethyl 4-bromo-3-methoxyindole-2-carboxylate
  参考文献：
  名称：

  Synthesis, pharmacology and therapeutic potential of 10-methoxypyrazino[1,2-a]indoles, partial agonists at the 5HT2C receptor

  摘要：

  A series of new 10-methoxypyrazino[1,2-a]indoles has been prepared and shown to be 5HT(2C) receptor ligands. The studied compounds 10a-j were found to act as partial agonists at the 5HT(2C) receptor, binding with high affinity and moderate selectivity versus 5HT(1A) and 5HT(2A) receptors, but inducing only a submaximal increase in phosphoinositol formation. Compound 10j was demonstrated to be active in animal models of obsessive-compulsive disorder, depression and panic anxiety.

  DOI：

  10.1016/s0223-5234(97)83976-1