9-(2-{¹⁸F}fluoroethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid benzylmethylamide | 1246453-48-4

• 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-{¹⁸F}fluoroethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid benzylmethylamide
• 英文别名: 9-(2-fluoro-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid benzyl-methyl-amide；N-benzyl-9-(2-(18F)fluoranylethyl)-N-methyl-1,2,3,4-tetrahydrocarbazole-4-carboxamide
• CAS: 1246453-48-4
• 化学式: C₂₃H₂₅FN₂O
• 分子量: 363.464
• InChiKey: FJAMEGHJYXTEHB-MIGPCILRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-bromo-2-hydroxy-cyclohex-1-enecarboxylic acid ethyl ester 在 草酰氯 、 palladium on activated charcoal 、 [⁽¹⁸⁾F]fluoride 、 水 、 氢气 、 potassium hydrogencarbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.17h， 生成 9-(2-{¹⁸F}fluoroethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid benzylmethylamide
  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

• IN VIVO IMAGING METHOD OF MOOD DISORDERS
  申请人：Jones Paul Alexander

  公开号：US20130177501A1

  公开（公告）日：2013-07-11

  The present invention provides a method useful in the diagnosis and/or monitoring of mood disorders wherein there is an abnormal expression of PBR. The method of the invention is useful in the differential diagnosis of said mood disorders and other conditions where there is no abnormal expression of PBR but where the symptoms may be similar to those of said mood disorder.

  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。本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的情况。
• IN VIVO IMAGING METHOD FOR CANCER
  申请人：Jones Paul Alexander

  公开号：US20130183240A1

  公开（公告）日：2013-07-18

  The present invention provides a method useful in the diagnosis and monitoring of cancer wherein there is an abnormal expression of PBR. The method of the invention is particularly useful in evaluating the severity of the cancer, e.g. PBR expression correlates with cell proliferation rates, metastatic potential, tumour aggressiveness, malignancy progression. The method of the invention can therefore be applied in the determination of likely disease progression and in making an associated prognosis. Furthermore, the method of the invention can find use in determining the likely success of certain therapeutic approaches, or in the evaluation of the efficacy of certain proposed new treatments.

  本发明提供了一种在癌症诊断和监测中有用的方法，其中PBR的表达异常。本发明的方法特别适用于评估癌症的严重程度，例如PBR的表达与细胞增殖率、转移潜力、肿瘤侵袭性、恶性进展相关。因此，本发明的方法可用于确定可能的疾病进展，并作出相关预后。此外，本发明的方法可用于确定某些治疗方法的可能成功率，或评估某些拟议新治疗方法的疗效。
• [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.