N-isopropyl-N-methyl-9-(2-fluoroethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxamide | 1360060-44-1

• 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: N-isopropyl-N-methyl-9-(2-fluoroethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxamide
• 英文别名: 9-(2-fluoroethyl)-N-methyl-N-propan-2-yl-1,2,3,4-tetrahydrocarbazole-4-carboxamide
• CAS: 1360060-44-1
• 化学式: C₁₉H₂₅FN₂O
• 分子量: 316.419
• InChiKey: BPGOUCVJJZHKQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-isopropyl-N-methyl-9-(2-fluoroethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxamide 在 Whelk-01 10X250 mm, 5μm, 100Å, type S,S 作用下， 以 甲醇 、 乙腈 为溶剂， 40.0 ℃ 、10.0 MPa 条件下， 生成 (S)-N-isopropyl-N-methyl-9-(2-fluoroethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxamide 、 (R)-N-isopropyl-N-methyl-9-(2-fluoroethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxamide
  参考文献：
  名称：

  [EN] CARBAZOLE COMPOUNDS FOR IN VIVO IMAGING
  [FR] COMPOSÉS DE TYPE CARBAZOLE POUR L'IMAGERIE IN VIVO

  摘要：

  本发明涉及体内成像，特别是体内成像转位蛋白（TSPO，以前称为外周苯二氮卓类受体）。提供了一种基于吲哚的体内成像试剂，克服了与已知TSPO结合放射示踪剂相关的问题。本发明还提供了一种在合成本发明的体内成像试剂中有用的前体化合物，以及一种合成所述前体化合物的方法。本发明的其他方面包括一种合成本发明的体内成像试剂的方法，包括使用本发明的前体化合物，用于执行该方法的试剂盒，以及用于执行该方法的自动化版本的盒子。此外，本发明提供了一种包括本发明的体内成像试剂的放射制剂组合物，以及使用该体内成像试剂的方法。

  公开号：

  WO2015040148A1
• 作为产物：
  描述：

  N-(2-氟乙基)苯胺 在 草酰氯 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 N-isopropyl-N-methyl-9-(2-fluoroethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxamide
  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

• CARBAZOLE COMPOUNDS FOR IN VIVO IMAGING
  申请人：GE HEALTHCARE LIMITED

  公开号：US20160214936A1

  公开（公告）日：2016-07-28

  The present invention concerns in vivo imaging and in particular in vivo imaging of translocator protein (TSPO, formerly known as the peripheral benzodiazepine receptor). An indole-based in vivo imaging agent is provided that overcomes problems relating to known TSPO-binding radiotracers. The present invention also provides 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 precursor compound. Other aspects of the invention include a method for the synthesis of the in vivo imaging agent of the invention comprising use of the precursor compound of the invention, a kit for carrying out said method, and a cassette for carrying out an automated version of said method. In addition, the invention provides a radiopharmaceutical composition comprising the in vivo imaging agent of the invention, as well as methods for the use of said in vivo imaging agent.

  本发明涉及体内成像，特别是体内成像转位蛋白（TSPO，曾被称为外周苯二氮平受体）。提供了一种基于吲哚的体内成像试剂，克服了与已知的TSPO结合放射性示踪剂相关的问题。本发明还提供了一种前体化合物，可用于合成本发明的体内成像试剂，以及合成所述前体化合物的方法。本发明的其他方面包括一种使用本发明的前体化合物合成本发明的体内成像试剂的方法，用于执行该方法的工具包，以及用于执行该方法的自动化版本的盒式装置。此外，本发明还提供了一种包含本发明的体内成像试剂的放射性药物组合物，以及使用所述体内成像试剂的方法。
• US9951011B2
  申请人：——

  公开号：US9951011B2

  公开（公告）日：2018-04-24
• [EN] CARBAZOLE COMPOUNDS FOR IN VIVO IMAGING<br/>[FR] COMPOSÉS DE TYPE CARBAZOLE POUR L'IMAGERIE IN VIVO
  申请人：GE HEALTHCARE LTD

  公开号：WO2015040148A1

  公开（公告）日：2015-03-26

  The present invention concerns in vivo imaging and in particular in vivo imaging of translocator protein (TSPO, formerly known as the peripheral benzodiazepine receptor). An indole-based in vivo imaging agent is provided that overcomes problems relating to known TSPO-binding radiotracers. The present invention also provides 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 precursor compound. Other aspects of the invention include a method for the synthesis of the in vivo imaging agent of the invention comprising use of the precursor compound of the invention, a kit for carrying out said method, and a cassette for carrying out an automated version of said method. In addition, the invention provides a radiopharmaceutical composition comprising the in vivo imaging agent of the invention, as well as methods for the use of said in vivo imaging agent.

  本发明涉及体内成像，特别是体内成像转位蛋白（TSPO，以前称为外周苯二氮卓类受体）。提供了一种基于吲哚的体内成像试剂，克服了与已知TSPO结合放射示踪剂相关的问题。本发明还提供了一种在合成本发明的体内成像试剂中有用的前体化合物，以及一种合成所述前体化合物的方法。本发明的其他方面包括一种合成本发明的体内成像试剂的方法，包括使用本发明的前体化合物，用于执行该方法的试剂盒，以及用于执行该方法的自动化版本的盒子。此外，本发明提供了一种包括本发明的体内成像试剂的放射制剂组合物，以及使用该体内成像试剂的方法。
• [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.