6,7,8,9-tetrahydro-5H-pyrido[3,4-b]indole | 25797-02-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 6,7,8,9-tetrahydro-5H-pyrido[3,4-b]indole
• 英文别名: 2,3-Tetramethylen-1,6-diazainden；5,6,7,8-Tetrahydro-β-carbolin；6,7,8,9-tetrahydro-5H-β-carboline
• CAS: 25797-02-8
• 化学式: C₁₁H₁₂N₂
• 分子量: 172.23
• InChiKey: XLUKCVDNZMRJNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6,7,8,9-tetrahydro-5H-pyrido[3,4-b]indole 在 palladium on activated carbon 作用下， 以 二苯醚 为溶剂， 反应 0.66h， 以94%的产率得到9H-吡啶[3,4-b]吲哚
  参考文献：
  名称：

  A Unified Approach to the Isomeric α-, β-, γ-, and δ-Carbolines via their 6,7,8,9-Tetrahydro Counterparts

  摘要：

  A cross-coupling/reductive cyclization protocol has been employed in a unified approach to all four carbolines. So, for example, the 2-nitropyridine 8, which is readily prepared through an efficient palladium-catalyzed Ullmann cross-coupling reaction, is reductively cyclized under conventional conditions to give 6,7,8,9-tetrahydro-alpha-carboline that is itself readily aromatized to give alpha-carboline (1).

  DOI：

  10.1021/acs.joc.7b00323
• 作为产物：
  描述：

  4-碘-3-硝基吡啶 在 copper(l) iodide 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 palladium on activated carbon 、 氢气 、 铜 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 18.5h， 生成 6,7,8,9-tetrahydro-5H-pyrido[3,4-b]indole
  参考文献：
  名称：

  A Unified Approach to the Isomeric α-, β-, γ-, and δ-Carbolines via their 6,7,8,9-Tetrahydro Counterparts

  摘要：

  A cross-coupling/reductive cyclization protocol has been employed in a unified approach to all four carbolines. So, for example, the 2-nitropyridine 8, which is readily prepared through an efficient palladium-catalyzed Ullmann cross-coupling reaction, is reductively cyclized under conventional conditions to give 6,7,8,9-tetrahydro-alpha-carboline that is itself readily aromatized to give alpha-carboline (1).

  DOI：

  10.1021/acs.joc.7b00323

文献信息

• [EN] TETRAHYDROCARBOLINE DERIVATIVES AS EG5 INHIBITORS<br/>[FR] DÉRIVÉS DE TÉTRAHYDROCARBOLINE COMME INHIBITEURS DE L'EG5
  申请人：SANOFI SA

  公开号：WO2011084439A1

  公开（公告）日：2011-07-14

  The present invention relates to substituted tetrahydro-β-carbolines and substituted tetrahydro-γ-carbolines. This invention also relates to methods of making these compounds including novel intermediates. The compounds of this invention are inhibitors of Eg5 kinesin. Therefore, the compounds of this invention are useful as pharmaceutical agents, especially in the treatment and/or prevention of diseases.

  本发明涉及替代的四氢-β-咔啉和替代的四氢-γ-咔啉。本发明还涉及制备这些化合物的方法，包括新颖的中间体。本发明的化合物是Eg5肌动蛋白的抑制剂。因此，本发明的化合物在药物制剂中具有用途，特别是在治疗和/或预防疾病方面。
• Pyrrolo [2,3-C] Pyridine Compound, Process for Producing the Same, and Use
  申请人：Hasuoka Atsushi

  公开号：US20070293532A1

  公开（公告）日：2007-12-20

  Provision of a compound having a superior proton pump action, which shows an antiulcer activity and the like after conversion to an in vivo proton pump inhibitor, a production method thereof and use thereof. A pyrrolo[2,3-c]pyridine compound represented by the formula: wherein each symbol is as defined in the specification.

  提供一种具有卓越质子泵作用的化合物，经转化为体内质子泵抑制剂后，表现出抗溃疡活性等，其生产方法和用途。一种由以下式表示的吡咯并[2,3-c]吡啶化合物：其中每个符号如规范中所定义。
• Polyhydronorharman synthase inhibitors
  申请人：ELI LILLY AND COMPANY

  公开号：EP0665227A1

  公开（公告）日：1995-08-02

  Selected acid functional polyhydronorharman type derivatives effective as thromboxane synthase inhibitors having the formula: where R₁ and R₂ are monovalent radicals, -(La)- is a linking group of 4 to 8 chain atoms, and A is an acidic group.

  作为血栓素合成酶抑制剂有效的精选酸官能团多氢哈尔曼型衍生物，其分子式为 其中 R₁ 和 R₂ 为单价基，-(La)- 为 4 至 8 个链原子的连接基团，A 为酸性基团。
• PYRROLOÝ2,3-c¨PYRIDINE COMPOUND, PROCESS FOR PRODUCING THE SAME, AND USE
  申请人：Takeda Pharmaceutical Company Limited

  公开号：EP1787991A1

  公开（公告）日：2007-05-23

  Provision of a compound having a superior proton pump action, which shows an antiulcer activity and the like after conversion to an in vivo proton pump inhibitor, a production method thereof and use thereof. A pyrrolo[2,3-c]pyridine compound represented by the formula: wherein each symbol is as defined in the specification.

  提供一种具有优异质子泵作用的化合物，该化合物在转化为体内质子泵抑制剂后显示出抗溃疡活性等作用，及其生产方法和用途。 一种由式表示的吡咯并[2,3-c]吡啶化合物： 其中各符号如说明书中所定义。
• Tetrahydro-beta-carboline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0217737B1

  公开（公告）日：1991-08-14