8-Bromo-5-phenyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid ethyl ester | 73931-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 8-Bromo-5-phenyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid ethyl ester
• 英文别名: ethyl 8-bromo-5-phenyl-3,4-dihydro-1H-pyrido[4,3-b]indole-2-carboxylate
• CAS: 73931-16-5
• 化学式: C₂₀H₁₉BrN₂O₂
• 分子量: 399.287
• InChiKey: UFGGTWJGHHXBSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.47
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  8-Bromo-5-phenyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid ethyl ester 在 aluminium hydride 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.5h， 生成 8-Brom-5-phenyl-2-methyl-1,2,3,4-tetrahydro-γ-carbolin
  参考文献：
  名称：

  Neuroleptic activity in 5-aryltetrahydro-.gamma.-carbolines

  摘要：

  A series of 5-aryltetrahydro-gamma-carbolines was prepared by a novel N-arylation procedure and tested for neuroleptic activity in a rat antiamphetamine model. The systematic exploration of structural parameters leading to 8-fluoro-5-(4-fluorophenyl)-2-[4-hydroxy-4-(4-fluorophenyl)butyl]-2,3,5-tetrahydro-1H-pyrido[4,3-b]indole (CP-36,584, flutroline), a potent and long-acting neuroleptic compound, is described. These semirigid compounds provide a new, structurally distinct series with which to probe the conformational requirements for potent activity at the dopamine receptor.

  DOI：

  10.1021/jm00180a011
• 作为产物：
  描述：

  N-乙氧羰基-4-哌啶酮 在 sodium carbonate 、 copper(I) bromide 作用下， 以 乙醇 为溶剂， 反应 9.75h， 生成 8-Bromo-5-phenyl-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Neuroleptic activity in 5-aryltetrahydro-.gamma.-carbolines

  摘要：

  A series of 5-aryltetrahydro-gamma-carbolines was prepared by a novel N-arylation procedure and tested for neuroleptic activity in a rat antiamphetamine model. The systematic exploration of structural parameters leading to 8-fluoro-5-(4-fluorophenyl)-2-[4-hydroxy-4-(4-fluorophenyl)butyl]-2,3,5-tetrahydro-1H-pyrido[4,3-b]indole (CP-36,584, flutroline), a potent and long-acting neuroleptic compound, is described. These semirigid compounds provide a new, structurally distinct series with which to probe the conformational requirements for potent activity at the dopamine receptor.

  DOI：

  10.1021/jm00180a011

文献信息

• HARBERT C. A.; PLATTNER J. J.; WELCH W. M.; WEISSMAN A.; KOE B. K., J. MED. CHEM., 1980, 23, NO 6, 635-643
  作者：HARBERT C. A.、 PLATTNER J. J.、 WELCH W. M.、 WEISSMAN A.、 KOE B. K.

  DOI：——

  日期：——