4-[8-fluoro-5-(4-fluoro-phenyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-yl]-1-(4-fluoro-phenyl)-butan-1-one | 58038-77-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[8-fluoro-5-(4-fluoro-phenyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-yl]-1-(4-fluoro-phenyl)-butan-1-one
• 英文别名: 4-[8-fluoro-5-(4-fluorophenyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-2-yl]-1-(4-fluorophenyl)butan-1-one
• CAS: 58038-77-0
• 化学式: C₂₇H₂₃F₃N₂O
• 分子量: 448.488
• InChiKey: RWEZXMOANWKHPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-[8-fluoro-5-(4-fluoro-phenyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-yl]-1-(4-fluoro-phenyl)-butan-1-one 在 盐酸 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.5h， 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
• 作为产物：
  描述：

  8-氟-1,3,4,5-四氢-2H-吡啶基-[4,3-b]吲哚-2-羧酸乙酯 在 氢氧化钾 、 水 、 sodium carbonate 、 potassium iodide 、 copper(I) bromide 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 4-[8-fluoro-5-(4-fluoro-phenyl)-1,3,4,5-tetrahydro-pyrido[4,3-b]indol-2-yl]-1-(4-fluoro-phenyl)-butan-1-one
  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：——
• WELCH, W. M. ,, JR.
  作者：WELCH, W. M. ,, JR.

  DOI：——

  日期：——
• Neuroleptic activity in 5-aryltetrahydro-.gamma.-carbolines
  作者：Charles A. Harbert、Jacob J. Plattner、Willard M. Welch、Albert Weissman、B. Kenneth Koe

  DOI：10.1021/jm00180a011

  日期：1980.6

  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.