2-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole | 6208-42-0

• 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-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
• 英文别名: 2-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole；2-Aethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol；2-Ethyl-2,3,4,5-tetrahydro-1H-pyrido<4,3-b>indol；2-ethyl-1,3,4,5-tetrahydropyrido[4,3-b]indole
• CAS: 6208-42-0
• 化学式: C₁₃H₁₆N₂
• 分子量: 200.283
• InChiKey: MYUAGMGKBGUWEN-UHFFFAOYSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  340.0±32.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole 在 盐酸羟胺 、 potassium tert-butylate 、 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.25h， 生成 4-((2-ethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)N-hydroxybenzamide TFA
  参考文献：
  名称：

  Second-Generation Histone Deacetylase 6 Inhibitors Enhance the Immunosuppressive Effects of Foxp3+ T-Regulatory Cells

  摘要：

  Second-generation Tubastatin A analogues were synthesized and evaluated for their ability to inhibit selectively histone deacetylase 6 (HDAC6). Substitutions to the carboline cap group were well-tolerated with substitution at the 2-position of both beta- and gamma-carbolines being optimal for HDAC6 activity and selectivity. Some compounds in this series were determined to have subnanomolar activity at HDAC6 with more than 7000 fold selectivity for HDAC6 versus HDAC1. Selected compounds were then evaluated for their ability to augment the immunosuppressive effect of Foxp3+ regulatory T cells. All compounds tested were found to enhance the ability of regulatory T cells to inhibit the mitotic division of effector T cells both in vitro and in vivo, suggesting that further investigation into the use of these compounds for the treatment of autoimmune disorders is warranted.

  DOI：

  10.1021/jm200773h
• 作为产物：
  描述：

  苯肼 在 硫酸 、 palladium 10% on activated carbon 、 氢气 、 sodium cyanoborohydride 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 水 为溶剂， 20.0~70.0 ℃ 、101.33 kPa 条件下， 反应 29.0h， 生成 2-ethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole
  参考文献：
  名称：

  Second-Generation Histone Deacetylase 6 Inhibitors Enhance the Immunosuppressive Effects of Foxp3+ T-Regulatory Cells

  摘要：

  Second-generation Tubastatin A analogues were synthesized and evaluated for their ability to inhibit selectively histone deacetylase 6 (HDAC6). Substitutions to the carboline cap group were well-tolerated with substitution at the 2-position of both beta- and gamma-carbolines being optimal for HDAC6 activity and selectivity. Some compounds in this series were determined to have subnanomolar activity at HDAC6 with more than 7000 fold selectivity for HDAC6 versus HDAC1. Selected compounds were then evaluated for their ability to augment the immunosuppressive effect of Foxp3+ regulatory T cells. All compounds tested were found to enhance the ability of regulatory T cells to inhibit the mitotic division of effector T cells both in vitro and in vivo, suggesting that further investigation into the use of these compounds for the treatment of autoimmune disorders is warranted.

  DOI：

  10.1021/jm200773h

文献信息

• [EN] PYRIDO (4,3-B) INDOLES CONTAINING RIGID MOIETIES<br/>[FR] PYRIDO[4,3-B]INDOLES CONTENANT DES FRAGMENTS RIGIDES
  申请人：MEDIVATION TECHNOLOGIES INC

  公开号：WO2010051501A1

  公开（公告）日：2010-05-06

  This disclosure is directed to pyrido[4,3-b]indoles having rigid moieties. The compounds in one embodiment are pyrido[4,3-b]indoles having an unsaturated hydrocarbon moiety. The compounds in another embodiment are pyrido[4,3-b]indoles having a cycloalkyl, cycloalkenyl or heterocyclyl moiety. 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.

  本公开涉及具有刚性基团的吡啶并[4,3-b]吲哚化合物。在一个实施例中，这些化合物是具有不饱和碳氢基团的吡啶并[4,3-b]吲哚化合物。在另一个实施例中，这些化合物是具有环烷基、环烯基或杂环基团的吡啶并[4,3-b]吲哚化合物。还提供了包括这些化合物的药物组合物，以及使用这些化合物在各种治疗应用中的方法，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。
• [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。
• [EN] METHODS FOR PREPARING PYRIDYLETHYL-SUBSTITUTED CARBOLINES<br/>[FR] PROCÉDÉS POUR PRÉPARER DES CARBOLINES SUBSTITUÉES PAR PYRIDYLÉTHYLE
  申请人：MEDIVATION NEUROLOGY INC

  公开号：WO2009111540A1

  公开（公告）日：2009-09-11

  Methods of preparing pyridylethyl-substituted carbolines under reaction conditions that use fewer molar equivalents of MVP to produce the pyridylethyl-substituted carboline as compared to reported methods of preparing pyridylethyl-substituted carbolines using MVP are provided. Also provided are methods of preparing a pyridylethyl-substituted carboline using non-commercial MVP.

  提供了一种在反应条件下制备吡啶乙基取代的咔啉类化合物的方法，该方法使用较少的MVP摩尔当量来生产吡啶乙基取代的咔啉类化合物，与使用MVP制备吡啶乙基取代的咔啉类化合物的报道方法相比。还提供了使用非商业MVP制备吡啶乙基取代的咔啉类化合物的方法。
• Methods and compositions for treating Huntington's disease
  申请人：Hung David

  公开号：US20070117834A1

  公开（公告）日：2007-05-24

  The invention provides method for treating Huntington's disease, slowing the onset and/or development and/or progression of Huntington's disease or preventing the development of Huntington's disease using hydrogenated pyrido[4,3-b]indoles, including dimebon.

  这项发明提供了一种治疗亨廷顿病的方法，通过使用氢化吡啶并呋[4,3-b]吲哚类化合物，包括二甲苯胺，来减缓亨廷顿病的发病、发展和/或进展，或预防亨廷顿病的发展。
• Synthesis and biological activity of N-substituted tetrahydro-γ-carbolins bearing bis(dimethylamino)phenothiazine moiety
  作者：V. B. Sokolov、A. Yu. Aksinenko、T. A. Epishina、T. V. Goreva、V. V. Grigoriev、A. V. Gabrel´yan、S. O. Bachurin

  DOI：10.1007/s11172-015-0925-3

  日期：2015.3

  An approach for modification of biologically active N-substituted tetrahydro-γ-carbolines with bis(dimethylamino)phenothiazine moiety via the CsF-catalyzed reaction of γ-carbolines with 1-[3,7-bis(dimethylamino)phenothiazin-10-yl]propenone was developed. Effects of the synthesized compounds on neuronal NMDA receptors were examined by radioligand binding assay.

  开发了一种通过CsF催化的γ-喹啉与1-[3,7-双（维生素）氨基]苯噻嗪-10-基丙烯酮反应，来修饰生物活性N取代的四氢-γ-喹啉的方法。合成化合物对神经元NMDA受体的影响通过放射性配体结合实验进行了检验。