9-(2-benzyloxyethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carbonyl chloride | 1246453-67-7

• 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: 9-(2-benzyloxyethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carbonyl chloride
• 英文别名: 9-(2-benzyloxyethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethylamine；9-(2-(benzyloxy)ethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethylamide；N,N-diethyl-5-methoxy-9-(2-phenylmethoxyethyl)-1,2,3,4-tetrahydrocarbazole-4-carboxamide
• CAS: 1246453-67-7
• 化学式: C₂₇H₃₄N₂O₃
• 分子量: 434.579
• InChiKey: LZZMNMVFUAXBSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  43.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-(2-benzyloxyethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carbonyl chloride 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 异丙醇 为溶剂， 反应 18.1h， 生成 (R)-methanesulphonic acid 2-(4-diethylcarbamyl-5-methoxy-1,2,3,4-tetrahydrocarbazol-9-yl)ethyl ester
  参考文献：
  名称：

  In vivo imaging method of mood disorders

  摘要：

  本发明提供了一种在诊断和/或监测情绪障碍方面有用的方法，其中存在PBR异常表达。该发明的方法对于区分所述情绪障碍和其他情况有用，其他情况中PBR表达正常但症状可能类似于所述情绪障碍。

  公开号：

  US09168317B2
• 作为产物：
  描述：

  9-(2-benzyloxyethyl)-8-chloro-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid 在 草酰氯 、 palladium 10% on activated carbon 、 氢气 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 38.0h， 生成 9-(2-benzyloxyethyl)-5-methoxy-2,3,4,9-tetrahydro-1H-carbazole-4-carbonyl chloride
  参考文献：
  名称：

  [EN] ENANTIOMERIC SEPARATION AND PURIFICATION OF 2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-4-CARBOXYLIC ACID AMIDE DERIVATIVES
  [FR] SÉPARATION ET PURIFICATION ÉNANTIOMÉRIQUES DE DÉRIVÉS D'AMIDE D'ACIDE 2,3,4,9-TÉTRAHYDRO-1H-CARBAZOLE-4-CARBOXYLIQUE

  摘要：

  本发明提供了一种用于纯化环状吲哚化合物的方法，相比先前已知的方法具有优势。使用本发明的方法可以方便地制备这些化合物的高质量固体形式。

  公开号：

  WO2015007834A1

文献信息

• [EN] ENANTIOMERIC SEPARATION AND PURIFICATION OF 2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-4-CARBOXYLIC ACID AMIDE DERIVATIVES<br/>[FR] SÉPARATION ET PURIFICATION ÉNANTIOMÉRIQUES DE DÉRIVÉS D'AMIDE D'ACIDE 2,3,4,9-TÉTRAHYDRO-1H-CARBAZOLE-4-CARBOXYLIQUE
  申请人：GE HEALTHCARE LTD

  公开号：WO2015007834A1

  公开（公告）日：2015-01-22

  The present invention provides a method for the purification of cyclic indole compounds that provides advantages over previously-known methods. Using the method of the present invention allows for the facile preparation of a good quality solid form of these compounds.

  本发明提供了一种用于纯化环状吲哚化合物的方法，相比先前已知的方法具有优势。使用本发明的方法可以方便地制备这些化合物的高质量固体形式。
• Crystallization process of tricyclic indole derivatives
  申请人：GE Healthcare Limited

  公开号：US10709798B2

  公开（公告）日：2020-07-14

  A composition comprising a tricyclic indole compound. The composition has a higher purity and better impurity profile than known compositions comprising said tricyclic indole compound and as a consequence has superior properties, particularly when said compound is destined for use in vivo as a therapeutic or diagnostic agent.

  一种包含三环吲哚化合物的组合物。与包含所述三环吲哚化合物的已知组合物相比，该组合物具有更高的纯度和更好的杂质分布，因此具有更优越的特性，特别是当所述化合物用于体内治疗或诊断时。
• [18F]GE-180: A novel fluorine-18 labelled PET tracer for imaging Translocator protein 18kDa (TSPO)
  作者：Harry Wadsworth、Paul A. Jones、Wai-Fung Chau、Clare Durrant、Naghmeh Fouladi、Joanna Passmore、Dennis O’Shea、Duncan Wynn、Veronique Morisson-Iveson、Amanda Ewan、Mikkel Thaning、Dimitrios Mantzilas、Ingvil Gausemel、Imtiaz Khan、Andrew Black、Michelle Avory、William Trigg

  DOI：10.1016/j.bmcl.2011.12.084

  日期：2012.2

  A series of tricyclic compounds have been synthesised and evaluated in vitro for affinity against Translocator protein 18 kDa (TSPO) and for preferred imaging properties. The most promising of the compounds were radiolabelled and evaluated in vivo to determine biodistribution and specificity for high expressing TSPO regions. Metabolite profiling in brain and plasma was also investigated. Evaluation in an autoradiography model of neuroinflammation was also carried out for the best compound, 12a ([F-18]GE-180). (C) 2011 Elsevier Ltd. All rights reserved.
• CRYSTALLIZATION PROCESS OF TRICYCLIC INDOLE DERIVATIVES
  申请人：GE Healthcare Limited

  公开号：US20150335766A1

  公开（公告）日：2015-11-26

  A composition comprising a tricyclic indole compound. The composition has a higher purity and better impurity profile than known compositions comprising said tricyclic indole compound and as a consequence has superior properties, particularly when said compound is destined for use in vivo as a therapeutic or diagnostic agent.
• [EN] CRYSTALLIZATION PROCESS OF TRICYCLIC INDOLE DERIVATIVES<br/>[FR] PROCÉDÉ DE CRISTALLISATION DE DÉRIVÉS D'INDOLE TRICYCLIQUES
  申请人：GE HEALTHCARE LTD

  公开号：WO2014083113A1

  公开（公告）日：2014-06-05

  The present invention relates to a composition comprising a tricyclic indole compound. The composition has a higher purity and better impurity profile than known compositions comprising said tricyclic indole compound and as a consequence has superior properties, particularly when said compound is destined for use in vivo as a therapeutic or diagnostic agent. Also provided by the present invention is a method to make the composition of the invention, a pharmaceutical composition comprising the composition of the invention, and use of the composition of the invention in a medical method.