2,8-dimethyl-5-[2-(6-trifluoromethylpyridin-3-yl)ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole | 1133879-35-2

• 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: 2,8-dimethyl-5-[2-(6-trifluoromethylpyridin-3-yl)ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
• 英文别名: 5-[2-(6-trifluoromethylpyridin-3-yl)ethyl]-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole；5-[2-(6-Trifluoromethylpyridin-3-yl)ethyl]-2,8-dimethyl2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole；2,8-dimethyl-5-[2-[6-(trifluoromethyl)pyridin-3-yl]ethyl]-3,4-dihydro-1H-pyrido[4,3-b]indole
• CAS: 1133879-35-2
• 化学式: C₂₁H₂₂F₃N₃
• 分子量: 373.421
• InChiKey: NJUCJKNZVOVJRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,8-dimethyl-5-[2-(6-trifluoromethylpyridin-3-yl)ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 以92%的产率得到5-[2-(6-trifluoromethylpyridin-3-yl)ethyl]-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole hydrochloride
  参考文献：
  名称：

  Fluorinated γ-carbolines as agents for delaying cognitive and motor dysfunctions in a transgenic model of neurodegenerative disorders

  摘要：

  通过在 2,6-二甲基-2,3,4,5-四氢-γ-咔啉中加入氟化乙烯基吡啶，合成了γ-咔啉衍生物。研究了在 5xFAD 转基因小鼠（脑淀粉样变性诱导的神经退行性疾病模型）中反复腹腔注射合成的衍生物对运动和认知功能障碍进展的影响，并将其与 Dimebon 进行了比较。

  DOI：

  10.1007/s11172-020-2833-4
• 作为产物：
  描述：

  2-(trifluoromethyl)-5-vinylpyridine 、 2,8-二甲基-2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚 在 对苯二酚 、 cesium fluoride 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以75%的产率得到2,8-dimethyl-5-[2-(6-trifluoromethylpyridin-3-yl)ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  Fluorinated γ-carbolines as agents for delaying cognitive and motor dysfunctions in a transgenic model of neurodegenerative disorders

  摘要：

  通过在 2,6-二甲基-2,3,4,5-四氢-γ-咔啉中加入氟化乙烯基吡啶，合成了γ-咔啉衍生物。研究了在 5xFAD 转基因小鼠（脑淀粉样变性诱导的神经退行性疾病模型）中反复腹腔注射合成的衍生物对运动和认知功能障碍进展的影响，并将其与 Dimebon 进行了比较。

  DOI：

  10.1007/s11172-020-2833-4

文献信息

• COMPOUNDS AND METHODS FOR TREATMENT OF HYPERTENSION
  申请人：Medivation Technologies, Inc.

  公开号：US20150266884A1

  公开（公告）日：2015-09-24

  Hydrogenated pyrido[4,3-b]indoles, pyrido[3,4-b]indoles and azepino[4,5-b]indoles are described. The compounds may bind to and are adrenergic receptor α 2B antagonists. The compounds may also bind to and antagonize adrenergic receptor α 1B . The compounds may find use in therapy, e.g., to (i) reduce blood pressure and/or (ii) promote renal blood flow and/or (iii) decrease or inhibit sodium reabsorption. The compounds may also be used to treat diseases or conditions that are, or are expected to be, responsive to a decrease in blood pressure. Use of the compounds to treat cardiovascular and renal disorders is particularly described.

  氢化吡啶并[4,3-b]吲哚，吡啶[3,4-b]吲哚和氮杂七元[4,5-b]吲哚被描述。这些化合物可能与肾上腺素受体α2B结合并拮抗。这些化合物也可能与肾上腺素受体α1B结合并拮抗。这些化合物可能在治疗中发挥作用，例如（i）降低血压和/或（ii）促进肾脏血流和/或（iii）减少或抑制钠重吸收。这些化合物也可用于治疗对降低血压有反应或预期会有反应的疾病或症状。特别描述了使用这些化合物治疗心血管和肾脏疾病。
• [EN] NEW TETRACYCLIC COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS TÉTRACYCLIQUES
  申请人：MEDIVATION TECHNOLOGIES INC

  公开号：WO2009055828A1

  公开（公告）日：2009-04-30

  This disclosure relates to new tetracyclic compounds that may be used to modulate a histamine receptor in an individual. The compounds in one embodiment are tetracyclic [4,3- b]indoles. Pharmaceutical compositions comprising the compounds are also provided, as are methods of using the compounds in a variety of therapeutic applications, including the treatment of a cognitive disorder, psychotic disorder, neurotransmitter-mediated disorder and/or a neuronal disorder.

  这项披露涉及可能用于调节个体组织胺受体的新四环化合物。在一个实施例中，这些化合物是四环[4,3- b]吲哚类化合物。此外还提供了包含这些化合物的药物组合物，以及使用这些化合物进行各种治疗应用的方法，包括治疗认知障碍、精神障碍、神经递质介导的障碍和/或神经元障碍。
• Fluoro-containing derivatives of hydrogenated pyrido[4,3-b]indoles with neuroprotective and cognition enhancing properties, process for preparing, and use
  申请人：Aksinenko Alexey

  公开号：US20090221627A1

  公开（公告）日：2009-09-03

  Some exemplary embodiments comprise fluoro-containing derivatives of pyrido[4,3-b]indoles (and exemplary methods of making the same) that may be administered to a mammal (including a human) in an effective amount for potential use in the treatment or prophylaxis of neurological disorders including AD, mild cognitive impairment, senile and vascular dementia, HD, ALS, Parkinson's disease, AIDS-related dementia, ischaemic cerebral pathologies, neuropathic pain, ADHD (attention deficit disorder/hyperactivity syndrome), eating disorders such as anorexia and bulimia, panic attacks, withdrawal from drug abuse such as cocaine, ethanol, nicotine and benzodiazepines, schizophrenia (in particular the cognitive deficit of schizophrenia), stroke and also disorders associated with spinal trauma and/or head injury. These derivatives may also be useful for the treatment of borderline personality disorder, obesity, and for use as geroprotectors. The compounds may also be used as “pharmacological tools” for an investigation of the mechanism of protection against neurodegeneration disorders in vivo or in vitro.

  有些典型实施例包括含氟的吡啶并[4,3-b]吲哚衍生物（以及制备这些衍生物的典型方法），可在有效剂量下用于治疗或预防神经系统疾病，包括AD，轻度认知障碍，老年性和血管性痴呆，HD，ALS，帕金森病，艾滋病相关痴呆，缺血性脑病，神经病性疼痛，注意力缺陷/多动症，饮食失调，如厌食症和贪食症，惊恐发作，戒毒如可卡因、乙醇、尼古丁和苯二氮平的戒断，精神分裂症（尤其是精神分裂症的认知缺陷），中风以及与脊髓创伤和/或头部损伤相关的疾病。这些衍生物也可用于治疗边缘人格障碍、肥胖症，并用作老年保护剂。这些化合物还可用作体内或体外神经退行性疾病保护机制的“药理学工具”。
• Tetracyclic compounds
  申请人：HUNG David T.

  公开号：US20090239854A1

  公开（公告）日：2009-09-24

  This disclosure relates to new tetracyclic compounds that may be used to modulate a histamine receptor in an individual. The compounds in one embodiment are tetracyclic [4,3-b]indoles. Pharmaceutical compositions comprising the compounds are also provided, as are methods of using the compounds in a variety of therapeutic applications, including the treatment of a cognitive disorder, psychotic disorder, neurotransmitter-mediated disorder and/or a neuronal disorder.

  本公开涉及新的四环化合物，可用于调节个体中的组胺受体。在一种实施例中，该化合物为四环[4,3-b]吲哚。还提供了包含该化合物的药物组合物，以及使用该化合物进行各种治疗应用的方法，包括治疗认知障碍、精神障碍、神经递质介导的障碍和/或神经元障碍。
• FLUORO-CONTAINING DERIVATIVES OF HYDROGENATED PYRIDO[4,3-B]INDOLES WITH NEUROPROTECTIVE AND COGNITION ENHANCING PROPERTIES, PROCESS FOR PREPARING, AND USE
  申请人：Aksinenko Alexey

  公开号：US20100056790A1

  公开（公告）日：2010-03-04

  Some exemplary embodiments comprise fluoro-containing derivatives of pyrido[4,3-b]indoles (and exemplary methods of making the same) that may be administered to a mammal (including a human) in an effective amount for potential use in the treatment or prophylaxis of neurological disorders including AD, mild cognitive impairment, senile and vascular dementia, HD, ALS, Parkinson's disease, AIDS-related dementia, ischaemic cerebral pathologies, neuropathic pain, ADHD (attention deficit disorder/hyperactivity syndrome), eating disorders such as anorexia and bulimia, panic attacks, withdrawal from drug abuse such as cocaine, ethanol, nicotine and benzodiazepines, schizophrenia (in particular the cognitive deficit of schizophrenia), stroke and also disorders associated with spinal trauma and/or head injury. These derivatives may also be useful for the treatment of borderline personality disorder, obesity, and for use as geroprotectors. The compounds may also be used as “pharmacological tools” for an investigation of the mechanism of protection against neurodegeneration disorders in vivo or in vitro.

  一些示范性实施例包括含氟的吡啶并[4,3-b]吲哚衍生物（以及制备这些衍生物的示范性方法），可在有效剂量下用于哺乳动物（包括人类），用于潜在治疗或预防神经系统疾病，包括AD，轻度认知障碍，老年性和血管性痴呆，HD，ALS，帕金森病，艾滋病相关痴呆，缺血性脑病，神经病性疼痛，ADHD（注意力缺陷障碍/多动症），进食障碍，如厌食症和贪食症，惊恐发作，戒断可卡因，乙醇，尼古丁和苯二氮卓类药物滥用，精神分裂症（特别是精神分裂症认知缺陷），中风以及与脊髓创伤和/或头部损伤相关的疾病。这些衍生物还可用于治疗边缘人格障碍，肥胖症，并用作老年保护剂。这些化合物还可用作“药理学工具”，用于体内或体外研究保护神经退行性疾病的机制。