ethyl 8-methoxy-1,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate | 63277-55-4

• 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: ethyl 8-methoxy-1,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate
• 英文别名: ethyl 1,3,4,5-tetrahydro-8-methoxy-2H-pyrido[4,3-b]indole-2-carboxylate；8-methoxy-1,3,4,5-tetrahydro-pyrido[4,3-b]indole-2-carboxylic acid ethyl ester；ethyl 8-methoxy-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate；ethyl 8-methoxy-1,3,4,5-tetrahydropyrido[4,3-b]indole-2-carboxylate
• CAS: 63277-55-4
• 化学式: C₁₅H₁₈N₂O₃
• mdl: MFCD03408368
• 分子量: 274.32
• InChiKey: BMOAZFYVGHVGGC-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C(Solvent: Ethanol)
• 沸点：
  450.693±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.259±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 8-methoxy-1,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-2(5H)-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8-甲氧基-2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚
  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：

  4-甲氧基苯肼盐酸盐 、 N-乙氧羰基-4-哌啶酮 以 乙醇 为溶剂， 反应 2.0h， 以60%的产率得到ethyl 8-methoxy-1,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate
  参考文献：
  名称：

  8-取代的四氢-γ-咔啉的合成

  摘要：

  使用催化或热方法，将Fischer反应应用于具有供电子或吸电子基团的8-取代的四氢-γ-咔啉的合成。反应条件必须根据哌啶酮的N 1取代基的性质而变化。当芳基肼上的释放基团和哌啶酮的氮上的苄基取代基存在时，观察到最好的结果。在软酸性条件下观察到带有取代基的咔啉的形成；在其他情况下，反应在ended水平结束或没有发生。

  DOI：

  10.1002/jhet.5570430308

文献信息

• Synthesis of 8-substituted tetrahydro-γ-carbolines
  作者：Alexandre Bridoux、Laurence Goossens、Raymond Houssin、Jean-Pierre Héanichart

  DOI：10.1002/jhet.5570430308

  日期：2006.5

  The Fischer reaction is applied to the synthesis of 8-substituted tetrahydro-γ-carbolines with electron-donating or electron-withdrawing groups, using catalytic or thermal methods. The reaction conditions must be varied according to the nature of the N 1 substituent of the piperidone. The best results are observed when a releasing group is present on the arylhydrazine and a benzyl substituent on the

  使用催化或热方法，将Fischer反应应用于具有供电子或吸电子基团的8-取代的四氢-γ-咔啉的合成。反应条件必须根据哌啶酮的N 1取代基的性质而变化。当芳基肼上的释放基团和哌啶酮的氮上的苄基取代基存在时，观察到最好的结果。在软酸性条件下观察到带有取代基的咔啉的形成；在其他情况下，反应在ended水平结束或没有发生。
• [EN] NEW Na-SUBSTITUTED CARBOLINE COMPOUNDS USABLE FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES<br/>[FR] NOUVEAUX COMPOSÉS DE CARBOLINE SUBSTITUÉS PAR NA POUVANT ÊTRE UTILISÉS POUR LE TRAITEMENT DE MALADIES NEURODÉGÉNÉRATIVES
  申请人：ALZPROTECT

  公开号：WO2014207241A1

  公开（公告）日：2014-12-31

  The present invention relates to a compound according to Formula (III) or a pharmaceutically acceptable salt, solvate, clathrate, hydrate or polymorph thereof and its use.

  本发明涉及一种符合以下式（III）的化合物或其药用可接受的盐、溶剂合物、包合物、水合物或多形体及其用途。
• Carboline Compounds Usable in The Treatment of Neurodegenerative Diseases
  申请人：ALZPROTECT

  公开号：US20160152610A1

  公开（公告）日：2016-06-02

  The present invention relates to a compound according to Formula (A) or a pharmaceutically acceptable salt, solvate, clathrate, hydrate or polymorph thereof, and its use.

  本发明涉及一种具有以下化学式（A）的化合物或其药学上可接受的盐、溶剂化合物、包合物、水合物或多晶形式，以及其用途。
• LIGANDS OF 5-HT6 RECEPTORS, A PHARMACEUTICAL COMPOSITION, METHOD FOR THE PRODUCTION AND USE THEREOF
  申请人：Alla Chem, LLC.

  公开号：EP2184064A2

  公开（公告）日：2010-05-12

  The invention relates to novel ligands of 5-HT6 receptor, to a pharmaceutical composition containing said novel ligands of 5-HT6 receptor as active component and to novel medicaments used for humans and warm-blooded animals for treating diseases and conditions of central nervous system, in pathogenesis of which neuromediator systems induced by 5-HT6 receptors are playing an essential role. Azaheterocyclic compounds of the general formula 1 or racemates, or optical or geometrical isomers, or pharmaceutically acceptable salts and/or hydrates thereof are used as 5-HT6 ligands. Wherein R2 and R3 independently of each other represent an amino group substituent selected from hydrogen; substituted carbonyl; substituted aminocarbonyl; substituted aminothiocarbonyl; substituted sulphonyl; C1-C5-alkyl optionally substituted by: C6-C10-arylaminocarbonyl, heterocyclyl, C6-C10-arylaminocarbonyl, C6-C10-arylaminothiocarbonyl, C5-C10-azaheteroaryl, optionally substituted carboxyl, nitryl group, optionally substituted aryl; R1k represents from 1 to 3 substituents of cyclic system, independent of each other and selected from hydrogen, optionally substituted C1-C5-alkyl, C1-C5-alkoxy, C1-C5-alkenyl, C1-C5-alkynyl, halogen, trifluoromethyl, CN-group, carboxyl, optionally substituted aryl, optionally substituted heterocyclyl, substituted sulfonyl, optionally substituted carboxyl; the solid line accompanied by the dotted line (---) represents a single or a double bond; n=1,2 or 3.

  本发明涉及 5-HT6 受体的新型配体、含有所述 5-HT6 受体新型配体作为活性成分的药物组合物以及用于人类和温血动物治疗中枢神经系统疾病和病症的新型药物，在中枢神经系统疾病和病症的发病机制中，5-HT6 受体诱导的神经介导系统发挥着重要作用。 通式 1 的杂杂环化合物或外消旋体，或光学或几何异构体，或其药学上可接受的盐和/或水合物可用作 5-HT6 配体。 其中，R2 和 R3 相互独立地代表一个氨基取代基，该取代基选自氢；取代的羰基；取代的氨基羰基；取代的氨基硫代羰基；取代的磺酰基；任选被以下取代的 C1-C5- 烷基：C6-C10-芳基氨基羰基：C6-C10-芳基氨基羰基、杂环烷基、C6-C10-芳基氨基羰基、C6-C10-芳基氨基硫代羰基、C5-C10-氮杂环芳基、任选取代的羧基、硝基、任选取代的芳基；R1k 代表 1 至 3 个相互独立的环状体系取代基，选自氢、任选取代的 C1-C5- 烷基、C1-C5-烷氧基、C1-C5-烯基、C1-C5-炔基、卤素、三氟甲基、CN 基、羧基、任选取代的芳基、任选取代的杂环基、取代的磺酰基、任选取代的羧基；伴随虚线 (---) 的实线代表单键或双键；n=1、2 或 3。
• Neuroleptic activity in 5-aryltetrahydro-.gamma.-carbolines
  作者：Charles A. Harbert、Jacob J. Plattner、Willard M. Welch、Albert Weissman、B. Kenneth Koe

  DOI：10.1021/jm00180a011

  日期：1980.6

  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.