2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚-8-羧酸 | 929345-60-8

• 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: 2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚-8-羧酸
• 英文名称: 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylic acid
• 英文别名: 1H,2H,3H,4H,5H-Pyrido[4,3-b]indole-8-carboxylic acid
• CAS: 929345-60-8
• 化学式: C₁₂H₁₂N₂O₂
• mdl: MFCD09259345
• 分子量: 216.239
• InChiKey: UZNWFVREQIRICS-UHFFFAOYSA-N

物化性质

• 密度：
  1.375

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚-8-羧酸 在 sodium hydride 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 tert-butyl 5-(1H-imidazol-1-ylsulfonyl)-8-[(4-methylpiperidin-1-yl)carbonyl]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate
  参考文献：
  名称：

  γ-Carbolines: A novel class of cannabinoid agonists with high aqueous solubility and restricted CNS penetration

  摘要：

  An oral, peripherally restricted CB1/CB2 agonist could provide an interesting approach to treat chronic pain by harnessing the analgesic properties of cannabinoids but without the well-known central side effects. gamma-Carbolines are a novel class of potent mixed CB1/CB2 agonists characterized by attractive physicochemical properties including high aqueous solubility. Optimization of the series has led to the discovery of 29, which has oral activity in a rat inflammatory pain model and limited brain exposure at analgesic doses, consistent with a lower risk of CNS-mediated tolerability issues. (C) 2012 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2011.12.124
• 作为产物：
  描述：

  4-氧代哌啶酮盐酸盐 、 4-羧基苯肼盐酸盐 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚-8-羧酸
  参考文献：
  名称：

  Targeting Low-Druggability Bromodomains: Fragment Based Screening and Inhibitor Design against the BAZ2B Bromodomain

  摘要：

  Bromodomains are epigenetic reader domains that have recently become popular targets. In contrast to BET bromodomains, which have proven druggable, bromodomains from other regions of the phylogenetic tree have shallower pockets. We describe successful targeting of the challenging BAZ2B bromodomain using biophysical fragment screening and structure-based optimization of high ligand-efficiency fragments into a novel series of low-micromolar inhibitors. Our results provide attractive leads for development of BAZ2B chemical probes and indicate the whole family may be tractable.

  DOI：

  10.1021/jm401582c

文献信息

• PYRIDOINDOLE MODULATORS OF NMDA RECEPTOR AND ACETYLCHOLINESTERASE
  申请人：Gant Thomas G.

  公开号：US20100125085A1

  公开（公告）日：2010-05-20

  The present invention relates to new pyridoindole modulators of NMDA receptors, AMPA receptors, and/or L-type calcium channels, and/or inhibitors of acetylcholinesterase, pharmaceutical compositions thereof, and methods of use thereof.

  本发明涉及新的吡啶吲哚调节NMDA受体、AMPA受体和/或L型钙通道，和/或抑制乙酰胆碱酯酶的药物组合物，以及其使用方法。
• Novel Tetrahydro-1H-Pyrido[4,3-b] Indole Derivatives as CB1 Receptor Ligands
  申请人：Cheng Yun-Xing

  公开号：US20100113502A1

  公开（公告）日：2010-05-06

  Compounds of formulae I, or pharmaceutically acceptable salts thereof: wherein R 1 , R 2 and R 3 are as defined in the specification as well as salts and pharmaceutical compositions including the compounds are prepared. They are useful in therapy, in particular in the management of pain.

  化合物I的公式，或其药学上可接受的盐：其中R1、R2和R3如规范中所定义，以及包括这些化合物的盐和药物组合物已被制备。它们在治疗中很有用，特别是在疼痛管理方面。
• WO2008/36022
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2008/36021
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] TETRAHYDRO-LH-PYRIDO [3,4 -B] INDOLE DERIVATIVES AS CBL RECEPTOR LIGANDS<br/>[FR] DÉRIVÉS DE TÉTRAHYDRO-LH-PYRIDO [3,4 -B] INDOLE LIGANDS DU RÉCEPTEUR CBL
  申请人：ASTRAZENECA AB

  公开号：WO2008036021A1

  公开（公告）日：2008-03-27

  [EN] The present invention provides tetrahydro-lH-pyrido [3, 4- b] indole derivatives, processes for their preparation, pharmaceutical compositions containing them and their use in therapy. The compounds act as cannabinoid receptor ligands (CB1) and thus may be used in the treatment of pain, cancer, multiple sclerosis, Parkinson's disease, Huntington's chorea, Alzheimer's disease, anxiety disorders, gastrointestinal disorders and/or cardiovascular disorders.
  [FR] La présente invention concerne des dérivés de tétrahydro-lH-pyrido [3, 4- b] indole, des procédés de préparation de ceux-ci, des compositions pharmaceutiques les contenant et leur utilisation thérapeutique. Ces composés sont des ligands du récepteur des cannabinoïdes (CB1) et peuvent ainsi être utilisés dans le traitement de la douleur, du cancer, de la sclérose en plaques, de la maladie de Parkinson, de la chorée de Huntington, de la maladie d'Alzheimer, des troubles de l'anxiété, des troubles gastro-intestinaux et/ou des troubles cardiovasculaires.