8-fluoro-5-(4-fluorophenyl)-2-(6-aminohexyl)-1,2,3,4-tetrahydro-γ-carboline | 83545-87-3

• 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-(6-aminohexyl)-1,2,3,4-tetrahydro-γ-carboline
• 英文别名: 8-fluoro-5-(4-fluorophenyl)-2-(6-amino-1-hexyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole；6-[8-fluoro-5-(4-fluorophenyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-2-yl]hexan-1-amine
• CAS: 83545-87-3
• 化学式: C₂₃H₂₇F₂N₃
• 分子量: 383.484
• InChiKey: OOXWFLZHLKZKHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 8-fluoro-5-(4-fluorophenyl)-2-(6-aminohexyl)-1,2,3,4-tetrahydro-γ-carboline 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 N-[6-[8-fluoro-5-(4-fluorophenyl)-3,4-dihydro-1H-pyrido[4,3-b]indol-2-yl]hexyl]benzamide
  参考文献：
  名称：

  Neuroleptic activity of chiral trans-hexahydro-.gamma.-carbolines

  摘要：

  A series of trans-8-fluoro-5-(4-fluorophenyl)-2,3,4,4a,5, 9b-hexahydro-1H-pyrido[4,3-b]indoles with various N-2 substituents has been prepared and tested for neuroleptic activity [( 3H]spiroperidol binding and amphetamine antagonism). Several members of this series showed exceptional in vivo potency, especially the hydantoin derivatives 27-30. Resolution into the enantiomers showed that neuroleptic activity is associated with the 4aS,9bS absolute configuration. These rigid neuroleptics have been correlated with other rigid neuroleptics [(+)-dexclamol, Ro 22-1319] and can serve to further define the topography of the dopamine receptor.

  DOI：

  10.1021/jm00151a002
• 作为产物：
  描述：

  五氯戊氰 在 lithium aluminium tetrahydride 、 sodium carbonate 、 potassium iodide 作用下， 以 乙醚 为溶剂， 反应 91.5h， 生成 8-fluoro-5-(4-fluorophenyl)-2-(6-aminohexyl)-1,2,3,4-tetrahydro-γ-carboline
  参考文献：
  名称：

  Neuroleptic activity of chiral trans-hexahydro-.gamma.-carbolines

  摘要：

  A series of trans-8-fluoro-5-(4-fluorophenyl)-2,3,4,4a,5, 9b-hexahydro-1H-pyrido[4,3-b]indoles with various N-2 substituents has been prepared and tested for neuroleptic activity [( 3H]spiroperidol binding and amphetamine antagonism). Several members of this series showed exceptional in vivo potency, especially the hydantoin derivatives 27-30. Resolution into the enantiomers showed that neuroleptic activity is associated with the 4aS,9bS absolute configuration. These rigid neuroleptics have been correlated with other rigid neuroleptics [(+)-dexclamol, Ro 22-1319] and can serve to further define the topography of the dopamine receptor.

  DOI：

  10.1021/jm00151a002

文献信息

• Hexahydro-trans- and tetrahydropyridoindole neuroleptic agents
  申请人：Pfizer Inc.

  公开号：US04431649A1

  公开（公告）日：1984-02-14

  Derivatives of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]-indole and of (+)enantiomeric, mixtures of (+) and (-)enantiomeric or (.+-.)racemic 2,3,4,4a,5,9b-hexahydro-4a,9b-trans-1H-pyrido[4,3-b]indole, substituted at the 5-position with an aryl group and at the 2-position with a carbonylaminoalkyl group or an aminoalkyl group, are neuroleptic agents useful in the treatment of certain psychoses and neuroses.

  2,3,4,5-四氢-1H-吡啶[4,3-b]-吲哚及其(+)-对映体、(+)-和(-)-对映体混合物或(.+-.)-消旋2,3,4,4a,5,9b-六氢-4a,9b-顺-1H-吡啶[4,3-b]吲哚的衍生物，在5位取代芳基基团和2位取代羧酰氨基烷基团或氨基烷基团，是治疗某些精神病和神经症的神经元外药物。
• Hexahydro-trans-pyridoindole
  申请人：Pfizer Inc.

  公开号：US04432978A1

  公开（公告）日：1984-02-21

  Derivatives of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]-indole and of (+)enantiomeric, mixtures of (+) and (-)enantiomeric or (.+-.)racemic 2,3,4,4a,5,9b-hexahydro-4a,9b-trans-1H-pyrido[4,3-b]indole, substituted at the 5-position with an aryl group and at the 2-position with a carbonylaminoalkyl group or an aminoalkyl group, are neuroleptic agents useful in the treatment of certain psychoses and neuroses.

  2,3,4,5-四氢-1H-吡啶[4,3-b]-吲哚及其(+)-对映体、(+)-和(-)-对映体混合物或(.+-.)外消旋的2,3,4,4a,5,9b-六氢-4a,9b-顺式-1H-吡啶[4,3-b]吲哚的衍生物，在5位取代芳基基团和2位取代羰基氨基烷基团或氨基烷基团，是治疗某些精神病和神经症的神经阻滞剂。
• US4337250A
  申请人：——

  公开号：US4337250A

  公开（公告）日：1982-06-29
• US4427679A
  申请人：——

  公开号：US4427679A

  公开（公告）日：1984-01-24
• US4431646A
  申请人：——

  公开号：US4431646A

  公开（公告）日：1984-02-14