8-fluoro-5-(4-fluorophenyl)-2-<4-(4-fluorophenyl)but-3-enyl>-1,2,3,4-tetrahydro-γ-carboline | 73931-28-9

• 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-fluoro-5-(4-fluorophenyl)-2-<4-(4-fluorophenyl)but-3-enyl>-1,2,3,4-tetrahydro-γ-carboline
• 英文别名: 8-fluoro-5-(4-fluorophenyl)-2-[4-(4-fluorophenyl)but-3-enyl]-3,4-dihydro-1H-pyrido[4,3-b]indole;hydrochloride
• CAS: 73931-28-9
• 化学式: C₂₇H₂₃F₃N₂*ClH
• 分子量: 468.949
• InChiKey: UVAKRXKMIKBTSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.93
• 重原子数：
  33.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  8.17
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  8-fluoro-5-(4-fluorophenyl)-2-<4-(4-fluorophenyl)but-3-enyl>-1,2,3,4-tetrahydro-γ-carboline 在 platinum(IV) oxide 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 4.5h， 生成 8-Fluoro-5-(4-fluoro-phenyl)-2-[4-(4-fluoro-phenyl)-butyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
  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：

  4-氟苯肼盐酸盐 在 盐酸 、 氢氧化钾 、 lithium aluminium tetrahydride 、 水 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 、 copper(I) bromide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 37.16h， 生成 8-fluoro-5-(4-fluorophenyl)-2-<4-(4-fluorophenyl)but-3-enyl>-1,2,3,4-tetrahydro-γ-carboline
  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