1-(3,6-二氢-2H-吡咯并[2,3-e]吲哚-1-基)-乙酮 | 1026613-77-3

• 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
• 中文名称: 1-(3,6-二氢-2H-吡咯并[2,3-e]吲哚-1-基)-乙酮
• 英文名称: 1-(3,6-dihydro-2H-pyrrolo[2,3-e]indol-1-yl)ethanone
• CAS: 1026613-77-3
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: KOOXRLIJTNZNLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(3,6-二氢-2H-吡咯并[2,3-e]吲哚-1-基)-乙酮 、 碘甲烷 在 sodium hydride 作用下， 生成 1-(6-Methyl-2,3-dihydropyrrolo[2,3-e]indol-1-yl)ethanone
  参考文献：
  名称：

  Synthesis, Biological Activity, and Molecular Modeling Studies of Selective 5-HT_2C/2B Receptor Antagonists

  摘要：

  The synthesis and biological activity are reported for a series of analogues of the previously published indole urea 2 (SB-206553), designed to probe the 5-HT2C receptor binding site. Small molecule modeling studies have been used to define a region in space which is allowed at the 5-HT2C receptor but disallowed at the 5-HT2A receptor. In a complementary approach, docking of 2 into our model of the 5-HT2C receptor has allowed us to propose a novel primary binding interaction for this series of diaryl ureas, involving a potential double hydrogen-bonding interaction between the urea carbonyl oxygen of the ligand and two serine residues in the receptor. The difference of two valine residues in the 5-HT2C receptor for leucine residues in the 5-HT2A receptor is believed to account for the observed 5-HT2C/5-HT2A selectivity with 2.

  DOI：

  10.1021/jm960571v
• 作为产物：
  描述：

  1-乙酰基-6-氨基吲哚 在 potassium carbonate 、 三氟乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 85.0h， 生成 1-(3,6-二氢-2H-吡咯并[2,3-e]吲哚-1-基)-乙酮
  参考文献：
  名称：

  Synthesis, Biological Activity, and Molecular Modeling Studies of Selective 5-HT_2C/2B Receptor Antagonists

  摘要：

  The synthesis and biological activity are reported for a series of analogues of the previously published indole urea 2 (SB-206553), designed to probe the 5-HT2C receptor binding site. Small molecule modeling studies have been used to define a region in space which is allowed at the 5-HT2C receptor but disallowed at the 5-HT2A receptor. In a complementary approach, docking of 2 into our model of the 5-HT2C receptor has allowed us to propose a novel primary binding interaction for this series of diaryl ureas, involving a potential double hydrogen-bonding interaction between the urea carbonyl oxygen of the ligand and two serine residues in the receptor. The difference of two valine residues in the 5-HT2C receptor for leucine residues in the 5-HT2A receptor is believed to account for the observed 5-HT2C/5-HT2A selectivity with 2.

  DOI：

  10.1021/jm960571v

文献信息

• Synthesis, Biological Activity, and Molecular Modeling Studies of Selective 5-HT_2C/2B Receptor Antagonists
  作者：Ian T. Forbes、Steven Dabbs、D. Malcolm Duckworth、Peter Ham、Graham E. Jones、Frank D. King、Damian V. Saunders、Frank E. Blaney、Christopher B. Naylor、Gordon S. Baxter、Thomas P. Blackburn、Guy A. Kennett、Martyn D. Wood

  DOI：10.1021/jm960571v

  日期：1996.1.1

  The synthesis and biological activity are reported for a series of analogues of the previously published indole urea 2 (SB-206553), designed to probe the 5-HT2C receptor binding site. Small molecule modeling studies have been used to define a region in space which is allowed at the 5-HT2C receptor but disallowed at the 5-HT2A receptor. In a complementary approach, docking of 2 into our model of the 5-HT2C receptor has allowed us to propose a novel primary binding interaction for this series of diaryl ureas, involving a potential double hydrogen-bonding interaction between the urea carbonyl oxygen of the ligand and two serine residues in the receptor. The difference of two valine residues in the 5-HT2C receptor for leucine residues in the 5-HT2A receptor is believed to account for the observed 5-HT2C/5-HT2A selectivity with 2.