2-[2-[(5-bromo-2,3-dihydroindol-1-yl)methyl]-5-methoxy-1H-indol-3-yl]ethanamine | 1112054-67-7

• 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: 2-[2-[(5-bromo-2,3-dihydroindol-1-yl)methyl]-5-methoxy-1H-indol-3-yl]ethanamine
• CAS: 1112054-67-7
• 化学式: C₂₀H₂₂BrN₃O
• 分子量: 400.318
• InChiKey: DAOTZUNZXYUOSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-[2-[(5-bromo-2,3-dihydroindol-1-yl)methyl]-5-methoxy-1H-indol-3-yl]ethanamine 、 乙酸酐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以0.13 g的产率得到N-(2-{5-methoxy-2-[(5-bromo-2,3-dihydro-1H-indol-1-yl)-methyl]-1H-indol-3-yl}ethyl)acetamide
  参考文献：
  名称：

  2-[(2,3-Dihydro-1H-indol-1-yl)methyl]melatonin Analogues: A Novel Class of MT₂-Selective Melatonin Receptor Antagonists

  摘要：

  A novel series of 2-[(2,3-dihydro-1H-indol-1-yl)methyl]melatonin analogues has been prepared to probe the steric and electronic properties of the binding pocket of the MT2 receptor accommodating the "out-of-plane" substituent of MT2-selective antagonists. The acetamide (6b) bearing an usubstituted indoline moiety displayed an excellent binding affinity and selectivity toward the MT2-subtype (MT2, K-i = 1 nM; MT1, K-i = 115 nM), behaving as a competitive antagonist. 5-Me, 5-OMe, 5-Br, 6-NH2, and 6-NO2 substitution of the indoline moiety reduced both MT2 affinity and selectivity, indicating that hydrophobic interactions play a decisive role in binding the out-of-plane substituent. The cyclobutanecarboxamide (6e) showed a biphasic binding pattern at MT2 receptors, indicating the presence of two MT2 binding sites, a high affinity (K-i = 1 pM) and a low affinity (K-i = 148 nM), while MT1 binding affinity was very low (K-i = 1.4 mu M). Functional analysis of 6e revealed it to be an antagonist at MT1 receptors and a partial agonist, at best, at MT2 receptors.

  DOI：

  10.1021/jm800974d
• 作为产物：
  描述：

  {2-[(5-bromo-2,3-dihydro-1H-indol-1-yl)-carbonyl]-5-methoxy-1H-indol-3-yl}acetonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 生成 2-[2-[(5-bromo-2,3-dihydroindol-1-yl)methyl]-5-methoxy-1H-indol-3-yl]ethanamine
  参考文献：
  名称：

  2-[(2,3-Dihydro-1H-indol-1-yl)methyl]melatonin Analogues: A Novel Class of MT₂-Selective Melatonin Receptor Antagonists

  摘要：

  A novel series of 2-[(2,3-dihydro-1H-indol-1-yl)methyl]melatonin analogues has been prepared to probe the steric and electronic properties of the binding pocket of the MT2 receptor accommodating the "out-of-plane" substituent of MT2-selective antagonists. The acetamide (6b) bearing an usubstituted indoline moiety displayed an excellent binding affinity and selectivity toward the MT2-subtype (MT2, K-i = 1 nM; MT1, K-i = 115 nM), behaving as a competitive antagonist. 5-Me, 5-OMe, 5-Br, 6-NH2, and 6-NO2 substitution of the indoline moiety reduced both MT2 affinity and selectivity, indicating that hydrophobic interactions play a decisive role in binding the out-of-plane substituent. The cyclobutanecarboxamide (6e) showed a biphasic binding pattern at MT2 receptors, indicating the presence of two MT2 binding sites, a high affinity (K-i = 1 pM) and a low affinity (K-i = 148 nM), while MT1 binding affinity was very low (K-i = 1.4 mu M). Functional analysis of 6e revealed it to be an antagonist at MT1 receptors and a partial agonist, at best, at MT2 receptors.

  DOI：

  10.1021/jm800974d