8-氯-2-甲基-2,3,4,5-四氢-1H-吡啶并[4,3-B]吲哚 | 17223-45-9

• 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
• 中文名称: 8-氯-2-甲基-2,3,4,5-四氢-1H-吡啶并[4,3-B]吲哚
• 英文名称: 8-chloro-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole
• 英文别名: 8-chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole；8-chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole；2-Methyl-8-chlor-2,3,4,5-tetrahydro-1H-pyrido<4,3-b>indol；8-Chlor-2-methyl-1,3,4,5-tetrahydro-2H-pyrido<4,3-b>indol；8-Chlor-2-methyl-1,2,3,4-tetrahydro-γ-carbolin；8-chloro-2-methyl-1,3,4,5-tetrahydropyrido[4,3-b]indole
• CAS: 17223-45-9
• 化学式: C₁₂H₁₃ClN₂
• 分子量: 220.702
• InChiKey: KFCWIHUDWIRLEE-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  359.0±37.0 °C(Predicted)
• 密度：
  1.285±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  8-氯-2-甲基-2,3,4,5-四氢-1H-吡啶并[4,3-B]吲哚 在 potassium carbonate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 9-chloro-2,3-dimethyl-1,4,5,6-tetrahydrodiazepino[5,4-b]indole
  参考文献：
  名称：

  经由叶立德中间体将四氢-γ-咔啉转化为六氢[1,2]二氮杂[5,4- b ]吲哚。9-溴-2,3-二甲基-1,2,3,4,5,6-六氢[1,2]二氮杂[5,4- b ]吲哚的X射线晶体结构测定

  摘要：

  Ñ的2-甲基-2,3,4,5-四氢-1H-1 -Amination ħ -吡啶并[4,3- b ]吲哚用ñ -烷基- ö -tosylhydroxylamines随后碱处理，得到1,2,3,4- ，5,6-六氢-2,3-二烷基[1,2]二氮杂[5,4- b ]吲哚，其中之一的结构由光谱证据和X射线结构分析确定。

  DOI：

  10.1039/p19830001937
• 作为产物：
  描述：

  N-乙氧羰基-4-哌啶酮 在 aluminium hydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 2.25h， 生成 8-氯-2-甲基-2,3,4,5-四氢-1H-吡啶并[4,3-B]吲哚
  参考文献：
  名称：

  Neuroleptic activity in 5-aryltetrahydro-.gamma.-carbolines

  摘要：

  A series of 5-aryltetrahydro-gamma-carbolines was prepared by a novel N-arylation procedure and tested for neuroleptic activity in a rat antiamphetamine model. The systematic exploration of structural parameters leading to 8-fluoro-5-(4-fluorophenyl)-2-[4-hydroxy-4-(4-fluorophenyl)butyl]-2,3,5-tetrahydro-1H-pyrido[4,3-b]indole (CP-36,584, flutroline), a potent and long-acting neuroleptic compound, is described. These semirigid compounds provide a new, structurally distinct series with which to probe the conformational requirements for potent activity at the dopamine receptor.

  DOI：

  10.1021/jm00180a011

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。
• 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。
• Pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives and methods of use
  申请人：Medivation Technologies, Inc.

  公开号：US09211287B2

  公开（公告）日：2015-12-15

  This disclosure is directed to pyrido[4,3-b]indole and pyrido[3,4-b]indole derivatives. 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. The compounds may bind to and antagonize receptor α2B, α1B or α2A. 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, or to regulate blood glucose level, increase insulin secretion and treat diseases or conditions that are, or are expected to be, responsive to an increase in insulin production. The compounds may also be used to treat diseases or conditions that are expected to be responsive to a decrease in blood pressure. Use of the compounds to treat cardiovascular, renal disorders or type 2 diabetes is particularly described.

  本公开涉及吡啶并[4,3-b]吲哚和吡啶并[3,4-b]吲哚衍生物。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、神经递质介导的疾病和/或神经疾病。这些化合物可能结合并拮抗α2B、α1B或α2A受体。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，或调节血糖水平，增加胰岛素分泌并治疗疾病或病况，对增加胰岛素产生有响应或预期有响应的疾病或病况。这些化合物还可用于治疗预期对降低血压有响应的疾病或病况。特别描述了使用这些化合物治疗心血管、肾脏疾病或2型糖尿病的方法。
• Double “Open and Shut” Transformation of γ-Carbolines Triggered by Ammonium Salts: One-Pot Synthesis of Multiheterocyclic Compounds
  作者：Takumi Abe、Haruka Shimizu、Shiori Takada、Takahiro Tanaka、Mai Yoshikawa、Koji Yamada

  DOI：10.1021/acs.orglett.8b00332

  日期：2018.3.16

  A novel cascade reaction of indole-2,3-epoxide equivalents with γ-carbolines by utilizing a double “open and shut” transformation to access multiheterocyclic compounds containing both isotryptamines and pyrimido[1,6-a]indoles has been developed. This strategy utilizes the in situ formation of a bulky quaternary ammonium salt via ammonium exchange, which undergoes Hofmann elimination/vinylogous Man

  通过利用双重“开闭”转化来获得同时含有异色胺和嘧啶并[1,6- a ]吲哚的多杂环化合物，开发了吲哚-2,3-环氧当量与γ-咔啉的新型级联反应。该策略利用铵交换在原位形成庞大的季铵盐，该交换经历霍夫曼消除/葡萄酒曼尼希/复古曼尼希/环化级联序列。