2-Methyl-5-phenyl-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indol | 56756-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-Methyl-5-phenyl-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indol
• 英文别名: 2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole；2-Methyl-5-phenyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol；2,3,4,5-tetrahydro-2-methyl-5-phenyl-1H-pyrido[4,3-b]indole；2-Methyl-5-phenyl-2,3,4,5-tetrahydro-1H-pyrido-<4.3-b>-indol；5-Phenyl-2-methyl-1,2,3,4-tetrahydro-γ-carbolin；2-methyl-5-phenyl-3,4-dihydro-1H-pyrido[4,3-b]indole
• CAS: 56756-99-1
• 化学式: C₁₈H₁₈N₂
• 分子量: 262.354
• InChiKey: SYYHFBXFRBCBKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Methyl-5-phenyl-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indol 、 氨 生成 (4aS,9bR)-2-methyl-5-phenyl-3,4,4a,9b-tetrahydro-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  BERGER J. G.; TELLER S. R.; ADAMS C. D.; GUGGENBERGER L. J., TETRAHEDRON LETT. , 1975, NO 22-23, 1807-1810

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3,4,5-四氢-2H-吡啶并[4,3-b]吲哚-2-甲酸乙酯 在 aluminium hydride 、 sodium carbonate 、 copper(I) bromide 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 8.5h， 生成 2-Methyl-5-phenyl-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indol
  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

• Trans-hexahydro-pyrido-indoles
  申请人：Endo Laboratories, Inc.

  公开号：US04174453A1

  公开（公告）日：1979-11-13

  Certain trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido-[4,3-b]indoles are useful as analgesics and sedatives. Some are also useful as major (antipsychotics) and/or minor (anxiolytics) tranquilizers, muscle relaxants, or hypotensives. The compounds of this invention are made by (1) reaction of .DELTA..sup.4a,9b -tetrahydro precursors with borane/THF and (2) acidifying the reaction product by which it is reduced and hydrolyzed to form the corresponding trans-hexahydro compound.

  某些trans-2,3,4,4a,5,9b-六氢-1H-吡啶[4,3-b]吲哚具有镇痛和镇静作用。其中一些也可用作主要（抗精神病药物）和/或次要（抗焦虑药物）镇静剂、肌肉松弛剂或降压药。该发明的化合物是通过以下步骤制备的：（1）将.DELTA..sup.4a,9b -四氢前体与硼酸乙醚反应，（2）酸化反应产物，从而还原和水解形成相应的trans-六氢化合物。
• Pyridoindoles
  申请人：Endo Laboratories, Inc.

  公开号：US03991199A1

  公开（公告）日：1976-11-09

  Certain trans-2,3,4,4a,5,9b-hexahydro-1H-pyrido-[4,3-b] indoles useful as analgesics and sedatives. Some are also useful as major (antipsychotics) and/or minor (anxiolytics) tranquilizers, muscle relaxants, or hypotensives. The compounds of this invention are made by borane/THF reduction of .DELTA..sup.4a,9b -tetrahydro precursors, followed where necessary by dealkylation, alkylation and/or acylation/reduction.

  某些trans-2,3,4,4a,5,9b-六氢-1H-吡啶[4,3-b]吲哚可用作镇痛剂和镇静剂。其中一些还可用作主要（抗精神病药物）和/或次要（抗焦虑药物）镇静剂、肌肉松弛剂或降压药物。本发明的化合物是通过对.DELTA..sup.4a,9b-四氢前体的硼烷/THF还原制备的，必要时进行脱烷基、烷基化和/或酰化/还原。
• NEW 2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLE COMPOUNDS AND METHODS OF USE THEREOF
  申请人：Hung David T.

  公开号：US20100022580A1

  公开（公告）日：2010-01-28

  This disclosure relates to new tricyclic compounds that may be used to modulate a histamine receptor in an individual. Compounds are described, including new 2,3,4,5-tetrahydro- 1 H-pyrido[4,3-b]indole compounds. Pharmaceutical compositions comprising the compounds are also provided, as are methods of using the compounds in a variety of therapeutic applications, including the treatment of a cognitive disorder, psychotic disorder, neurotransmitter-mediated disorder and/or a neuronal disorder.

  本公开涉及新的三环化合物，可用于调节个体中的组胺受体。其中描述了化合物，包括新的2,3,4,5-四氢-1H-吡啶[4,3-b]吲哚化合物。还提供了包含该化合物的制药组合物，以及使用该化合物治疗各种治疗应用的方法，包括治疗认知障碍、精神病性障碍、神经递质介导的障碍和/或神经元障碍。
• 2,3,4,5-TETRAHYDRO-1H-PYRIDO[4,3-B]INDOLE COMPOUNDS AND METHODS OF USE THEREOF
  申请人：Medivation Technologies, Inc.

  公开号：US20130190347A1

  公开（公告）日：2013-07-25

  This disclosure relates to new tricyclic compounds that may be used to modulate a histamine receptor in an individual. Compounds are described, including new 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole compounds. Pharmaceutical compositions comprising the compounds are also provided, as are methods of using the compounds in a variety of therapeutic applications, including the treatment of a cognitive disorder, psychotic disorder, neurotransmitter-mediated disorder and/or a neuronal disorder.

  本公开涉及新的三环化合物，可用于调节个体中的组胺受体。其中包括新的2,3,4,5-四氢-1H-吡啶[4,3-b]吲哚化合物。此外还提供了包含这些化合物的制药组合物，以及使用这些化合物治疗各种治疗应用的方法，包括治疗认知障碍、精神障碍、神经递质介导的障碍和/或神经元障碍。
• NEW 2,3,4,5-TETRAHYDRO-1H-PYRIDO [4,3-B] INDOLE COMPOUNDS AND METHODS OF USE THEREOF
  申请人：MEDIVATION TECHNOLOGIES, INC.

  公开号：US20130190348A1

  公开（公告）日：2013-07-25

  This disclosure relates to new tricyclic compounds that may be used to modulate a histamine receptor in an individual. Compounds are described, including new 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole compounds. Pharmaceutical compositions comprising the compounds are also provided, as are methods of using the compounds in a variety of therapeutic applications, including the treatment of a cognitive disorder, psychotic disorder, neurotransmitter-mediated disorder and/or a neuronal disorder.

  本披露涉及新的三环化合物，可用于调节个体中的组胺受体。本文描述了包括新的2,3,4,5-四氢-1H-吡啶[4,3-b]吲哚化合物在内的化合物。还提供了包括该化合物的药物组合物，以及使用该化合物在各种治疗应用中的方法，包括治疗认知障碍、精神障碍、神经递质介导的障碍和/或神经元障碍。