2-[4-(Azepane-1-carbonyl)-1,2,3,4-tetrahydrocarbazol-9-yl]ethyl methanesulfonate | 1360061-26-2

• 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: 2-[4-(Azepane-1-carbonyl)-1,2,3,4-tetrahydrocarbazol-9-yl]ethyl methanesulfonate
• CAS: 1360061-26-2
• 化学式: C₂₂H₃₀N₂O₄S
• 分子量: 418.557
• InChiKey: RRWAOVTYQPNIOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[4-(Azepane-1-carbonyl)-1,2,3,4-tetrahydrocarbazol-9-yl]ethyl methanesulfonate 在 [⁽¹⁸⁾F]fluoride 、 potassium hydrogencarbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 生成 azepan-1-yl-[9-(2-(18F)fluoranylethyl)-1,2,3,4-tetrahydrocarbazol-4-yl]methanone
  参考文献：
  名称：

  [18F]GE-180: A novel fluorine-18 labelled PET tracer for imaging Translocator protein 18kDa (TSPO)

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.12.084
• 作为产物：
  描述：

  3-bromo-2-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester 在 草酰氯 、 palladium on activated charcoal 、 水 、 氢气 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 生成 2-[4-(Azepane-1-carbonyl)-1,2,3,4-tetrahydrocarbazol-9-yl]ethyl methanesulfonate
  参考文献：
  名称：

  [18F]GE-180: A novel fluorine-18 labelled PET tracer for imaging Translocator protein 18kDa (TSPO)

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.12.084

文献信息

• INDOLE DERIVATIVES
  申请人：GE HEALTHCARE LIMITED

  公开号：US20140364615A1

  公开（公告）日：2014-12-11

  An indole-based in vivo imaging agent is provided by the present invention that binds with high affinity to PBR, has good uptake into the brain following administration, and which has good selective binding to PBR. The invention also includes a precursor compound useful in the synthesis of the in vivo imaging agent of the invention, as well as a method for synthesis of said in vivo imaging agent comprising use of said precursor compound, and a kit for carrying out said method. Also provided is a cassette for automated synthesis of the in vivo imaging agent. Further aspects of the invention include a radiopharmaceutical composition comprising the in vivo imaging agent of the invention, and methods for the use of said in vivo imaging agent.

  本发明提供了一种基于吲哚的体内成像剂，它与PBR具有高亲和力，且在给药后具有良好的大脑摄取能力，并且对PBR具有很好的选择性结合。本发明还包括一种在合成该体内成像剂中有用的前体化合物，以及一种合成所述体内成像剂的方法，包括使用所述前体化合物，并提供了用于执行该方法的工具包。此外，本发明还提供了一种用于自动合成体内成像剂的盒式装置。本发明的其他方面包括包含所述体内成像剂的放射性药物组合物，以及使用所述体内成像剂的方法。
• Tricyclic indole derivatives as PBR ligands
  申请人：GE Healthcare Limited

  公开号：EP2411362B1

  公开（公告）日：2017-05-31
• US8790619B2
  申请人：——

  公开号：US8790619B2

  公开（公告）日：2014-07-29
• US9220795B2
  申请人：——

  公开号：US9220795B2

  公开（公告）日：2015-12-29
• [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.