methanesulfonic acid 2-(4-diethylcarbamoyl-5-fluoro-1,2,3,4-tetrahydro-carbazol-9-yl)-ethyl ester | 1246454-00-1

• 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: methanesulfonic acid 2-(4-diethylcarbamoyl-5-fluoro-1,2,3,4-tetrahydro-carbazol-9-yl)-ethyl ester
• 英文别名: methanesulfonic acid 2-(4-diethylcarbamoyl-5-fluoro-1,2,3,4-tetrahydrocarbazol-9-yl)ethyl ester；2-[4-(Diethylcarbamoyl)-5-fluoro-1,2,3,4-tetrahydrocarbazol-9-yl]ethyl methanesulfonate
• CAS: 1246454-00-1
• 化学式: C₂₀H₂₇FN₂O₄S
• 分子量: 410.51
• InChiKey: OHFNJAAYHOLKTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methanesulfonic acid 2-(4-diethylcarbamoyl-5-fluoro-1,2,3,4-tetrahydro-carbazol-9-yl)-ethyl ester 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 5-fluoro-9-(2-[¹⁸F]fluoro-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethylamide
  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 methanesulfonic acid 2-(4-diethylcarbamoyl-5-fluoro-1,2,3,4-tetrahydro-carbazol-9-yl)-ethyl ester
  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
• 作为试剂：
  描述：

  5-fluoro-9-(2-hydroxy-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethylamide 、 7-fluoro-9-(2-hydroxy-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid diethylamide 、 吡啶 、 甲基磺酰氯 在 盐酸 、 水 、 crude material 、 乙酸乙酯 、 methanesulfonic acid 2-(4-diethylcarbamoyl-7-fluoro-1,2,3,4-tetrahydro-carbazol-9-yl)-ethyl ester 、 methanesulfonic acid 2-(4-diethylcarbamoyl-5-fluoro-1,2,3,4-tetrahydro-carbazol-9-yl)-ethyl ester 作用下， 以 二氯甲烷 为溶剂， 反应 16.33h， 以21 mL/min) to afford 10 mg (1%) of methanesulfonic acid 2-(4-diethylcarbamoyl-7-fluoro-1,2,3,4-tetrahydro-carbazol-9-yl)-ethyl ester as a white solid and 30 mg (9%) of a mixture of methanesulfonic acid 2-(4-diethylcarbamoyl-7-fluoro-1,2,3,4-tetrahydro-carbazol-9-yl)-ethyl ester and methanesulfonic acid 2-(4-diethylcarbamoyl-5-fluoro-1,2,3,4-tetrahydro-carbazol-9-yl)-ethyl ester as a white solid的产率得到methanesulfonic acid 2-(4-diethylcarbamoyl-7-fluoro-1,2,3,4-tetrahydro-carbazol-9-yl)-ethyl ester
  参考文献：
  名称：

  IN VIVO IMAGING METHOD OF MOOD DISORDERS

  摘要：

  本发明提供了一种用于诊断和/或监测情绪障碍的方法，其中存在PBR异常表达。该发明的方法对于区分上述情绪障碍和其他症状类似于该情绪障碍但不存在PBR异常表达的情况非常有用。

  公开号：

  US20130177501A1

文献信息

• In vivo imaging method for cancer
  申请人：Jones Paul Alexander

  公开号：US09314541B2

  公开（公告）日：2016-04-19

  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, tumor 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的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，本发明的方法可以应用于确定可能的疾病进展，并作出相关的预后。此外，本发明的方法可以用于确定某些治疗方法的成功可能性，或评估某些提议的新治疗方法的有效性。
• In vivo imaging method of mood disorders
  申请人：Jones Paul Alexander

  公开号：US09168317B2

  公开（公告）日：2015-10-27

  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。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。
• 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。
• 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。
• ENANTIOMERIC SEPARATION AND PURIFICATION OF 2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-4-CARBOXYLIC ACID AMIDE DERIVATIVES
  申请人：GE HEALTHCARE LIMITED

  公开号：US20160168091A1

  公开（公告）日：2016-06-16

  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.

  一种用于纯化环状吲哚化合物的方法，相较于先前已知的方法具有优势。使用本发明的方法可以轻松制备这些化合物的高质量固态形式。