7‐fluoro‐2,3,4,5‐tetrahydro‐1H‐pyrido[4,3‐b]indole

• 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: 7‐fluoro‐2,3,4,5‐tetrahydro‐1H‐pyrido[4,3‐b]indole
• 英文别名: 7-fluoro-2,3,4,5-tetrahydro 1H-pyrido[4,3-b]indole；7-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole；7-Fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]-indole；7-fluoro-2,3,4,5-tetrahydropyrido[4,3-b]indole
• 化学式: C₁₁H₁₁FN₂
• 分子量: 190.22
• InChiKey: WZOXNYYEBXHSGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7‐fluoro‐2,3,4,5‐tetrahydro‐1H‐pyrido[4,3‐b]indole 、 二碳酸二叔丁酯 以 四氢呋喃 为溶剂， 以98%的产率得到tert-butyl 7-fluoro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of γ-carboline derivatives as potent and selective cysLT1 antagonists

  摘要：

  A gamma-carboline series of cysLT(1) receptor antagonists has been prepared. Some of the compounds show good potencies both, in vitro and in vivo, compared to the standard compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.094
• 作为产物：
  描述：

  ethyl 7-fluoro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate 在 potassium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 16.0h， 以87%的产率得到7‐fluoro‐2,3,4,5‐tetrahydro‐1H‐pyrido[4,3‐b]indole
  参考文献：
  名称：

  Synthesis and structure–activity relationships of γ-carboline derivatives as potent and selective cysLT1 antagonists

  摘要：

  A gamma-carboline series of cysLT(1) receptor antagonists has been prepared. Some of the compounds show good potencies both, in vitro and in vivo, compared to the standard compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.094

文献信息

• Novel Compound - 827
  申请人：Dossetter Alexander Graham

  公开号：US20090012077A1

  公开（公告）日：2009-01-08

  The present invention relates to compounds and compositions for treating diseases associated with cysteine protease activity. The compounds are reversible inhibitors of cysteine proteases, including cathepsins B, K, C, F, H, L, O, S, W and X. Of particular interest are diseases associated with Cathepsin K.

  本发明涉及用于治疗与半胱氨酸蛋白酶活性相关疾病的化合物和组合物。这些化合物是半胱氨酸蛋白酶的可逆抑制剂，包括卡特普辛B、K、C、F、H、L、O、S、W和X。特别感兴趣的是与卡特普辛K相关的疾病。
• [EN] 1, 3, 4, 5-TETRAHYDRO-2H-PYRIDO[4,3-B]INDOLE DERIVATIVES FOR THE TREATMENT, ALLEVIATION OR PREVENTION OF DISORDERS ASSOCIATED WITH TAU AGGREGATES LIKE ALZHEIMER'S DISEASE<br/>[FR] DÉRIVÉS DE 1,3,4,5-TÉTRAHYDRO-2H-PYRIDO[4,3-B]INDOLE POUR LE TRAITEMENT, LE SOULAGEMENT OU LA PRÉVENTION DE TROUBLES ASSOCIÉS À DES AGRÉGATS DE TAU COMME LA MALADIE D'ALZHEIMER
  申请人：AC IMMUNE SA

  公开号：WO2019134978A1

  公开（公告）日：2019-07-11

  The present invention relates to novel compounds that can be employed in the treatment, alleviation or prevention of a group of disorders and abnormalities associated with Tau (Tubulin associated unit) protein aggregates including, but not limited to, Neurofibrillary Tangles (NFTs), such as Alzheimer's disease (AD).

  本发明涉及一类新化合物，可用于治疗、缓解或预防与Tau蛋白聚集相关的一组疾病和异常，包括但不限于神经原纤维缠结（NFTs），如阿尔茨海默病（AD）。
• Biomimetic Oxidative Coupling Cyclization Enabling Rapid Construction of Isochromanoindolenines
  作者：Jinxiang Ye、Yuqi Lin、Qing Liu、Dekang Xu、Fan Wu、Bin Liu、Yu Gao、Haijun Chen

  DOI：10.1021/acs.orglett.8b02377

  日期：2018.9.7

  Herein, we report a biomimetic oxidative coupling cyclization strategy for the highly efficient functionalization of tetrahydrocarbolines (THCs). This process enables rapid access to complex isochromanoindolenine scaffolds in moderate to excellent yields. The reaction proceeds smoothly and rapidly (complete within minutes) in an open flask. This operationally simple protocol is scalable and compatible

  在这里，我们报告了仿生的氧化偶合环化策略的四氢呋喃（THCs）的高效功能化。该过程使得能够以中等至优异的产率快速获得复杂的异色氨酸吲哚骨架。在敞口烧瓶中，反应平稳快速地进行（数分钟内完成）。这种操作简单的协议具有可扩展性，并且与各种功能组兼容。还证明了药理学相关分子的后期功能化。
• <i>peri</i> ‐Xanthenoxanthene (PXX): a Versatile Organic Photocatalyst in Organic Synthesis
  作者：Cristofer Pezzetta、Andrea Folli、Oliwia Matuszewska、Damien Murphy、Robert W. M. Davidson、Davide Bonifazi

  DOI：10.1002/adsc.202100030

  日期：2021.10.19

  to be accessible: the β-arylation of cyclic ketones is successful when using a secondary amine as organocatalyst, while cross-coupling reactions of aryl halides with amines and thiols are obtained when using a Ni co-catalyst. Application to the efficient two-step synthesis of the expensive fluoro-tetrahydro-1H-pyrido[4,3-b]indole, a crucial synthetic intermediate for the investigational drug setipiprant

  近年来，光催化剂的不断发展，以满足对光氧化还原催化中光物理和氧化还原性能日益增长的需求，设计了复杂的结构或替代策略来获得高度还原或氧化系统。我们在此报告了使用peri- xanthenoxanthene (PXX)，一种简单且廉价的染料，作为一种有效的光催化剂。其高度还原的激发态可激活多种底物，从而引发有用的自由基反应。最初证明了基准转换，例如通过有机卤化物的光还原产生的有机自由基添加到自由基陷阱。还显示可以使用更复杂的双催化歧管：β当使用仲胺作为有机催化剂时，环酮的芳基化是成功的，而当使用 Ni 助催化剂时，芳基卤化物与胺和硫醇的交叉偶联反应是成功的。昂贵的氟-四氢-1 H-吡啶并[4,3- b ]吲哚的高效两步合成应用也已得到证实，该吲哚是研究药物塞替吡仑的关键合成中间体。
• [EN] NOVEL COMPOUNDS FOR THE TREATMENT, ALLEVIATION OR PREVENTION OF DISORDERS ASSOCIATED WITH TAU AGGREGATES<br/>[FR] NOUVEAUX COMPOSÉS POUR LE TRAITEMENT, LE SOULAGEMENT OU LA PRÉVENTION DE TROUBLES ASSOCIÉS À DES AGRÉGATS DE PROTÉINE TAU
  申请人：AC IMMUNE SA

  公开号：WO2020177952A1

  公开（公告）日：2020-09-10

  The present invention relates to novel compounds that can be employed in the treatment, alleviation or prevention of a group of disorders and abnormalities associated with Tau (Tubulin associated unit) protein aggregates including, but not limited to, Neurofibrillary Tangles (NFTs), such as Alzheimer's disease (AD).

  本发明涉及一种新型化合物，可用于治疗、缓解或预防与Tau（微管相关单元）蛋白聚集相关的一组疾病和异常，包括但不限于神经原纤维缠结（NFTs），如阿尔茨海默病（AD）。