1,3,4,5-四氢-吡啶并[4,3-b]吲哚-2,8-二羧酸 2-叔丁酯 | 300715-96-2

• 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
• 中文名称: 1,3,4,5-四氢-吡啶并[4,3-b]吲哚-2,8-二羧酸 2-叔丁酯
• 中文别名: 1,3,4,5-四氢-吡啶并[4,3-b]吲哚-2,8-二羧酸2-叔丁酯
• 英文名称: 2-(tert-butoxycarbonyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole-8-carboxylic acid
• 英文别名: 2-[(2-methylpropan-2-yl)oxycarbonyl]-1,3,4,5-tetrahydropyrido[4,3-b]indole-8-carboxylic acid
• CAS: 300715-96-2
• 化学式: C₁₇H₂₀N₂O₄
• mdl: MFCD04115223
• 分子量: 316.357
• InChiKey: LCLGLPDRQJBJET-UHFFFAOYSA-N

物化性质

• 沸点：
  528.5±50.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  82.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1,3,4,5-四氢-吡啶并[4,3-b]吲哚-2,8-二羧酸 2-叔丁酯 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-) 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-肼基苯甲酸 在 盐酸 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 1,3,4,5-四氢-吡啶并[4,3-b]吲哚-2,8-二羧酸 2-叔丁酯
  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

文献信息

• 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。
• WO2006/101434
  申请人：——

  公开号：——

  公开（公告）日：——
• Targeting Low-Druggability Bromodomains: Fragment Based Screening and Inhibitor Design against the BAZ2B Bromodomain
  作者：Fleur M. Ferguson、Oleg Fedorov、Apirat Chaikuad、Martin Philpott、Joao R. C. Muniz、Ildiko Felletar、Frank von Delft、Tom Heightman、Stefan Knapp、Chris Abell、Alessio Ciulli

  DOI：10.1021/jm401582c

  日期：2013.12.27

  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.
• NOVEL TETRAHYDRO-1H-PYRIDO [4,3-b] INDOLE DERIVATIVES AS CB1' RECEPTOR LIGANDS
  申请人：AstraZeneca AB

  公开号：EP1863810A1

  公开（公告）日：2007-12-12
• [EN] NOVEL TETRAHYDRO-1H-PYRIDO [4,3-b] INDOLE DERIVATIVES AS CB1' RECEPTOR LIGANDS<br/>[FR] NOUVEAUX DERIVES DE TETRAHYDRO-1H-PYRIDO [4,3-B]INDOLE UTILISES COMME LIGANDS DU RECEPTEUR CB1'
  申请人：ASTRAZENECA AB

  公开号：WO2006101434A1

  公开（公告）日：2006-09-28

  [EN] Compounds of Formulae I, or pharmaceutically acceptable salts thereof: wherein R¹, R² and R³ 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.
  [FR] L'invention concerne des composés de formule (I), ou des sels pharmaceutiquement acceptables desdits composés, dans laquelle R¹, R² et R³ sont tels que définis dans le mémorandum descriptif. Elle concerne également des sels et des compositions pharmaceutiques comprenant les composés, lesquels sont utiles en thérapie, en particulier pour l'apaisement de la douleur.