(2-benzyl-5-prop-2-enyl-3,4-dihydro-1H-pyrido[4,3-b]indol-8-yl)-(4-methylpiperidin-1-yl)methanone | 1361408-14-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2-benzyl-5-prop-2-enyl-3,4-dihydro-1H-pyrido[4,3-b]indol-8-yl)-(4-methylpiperidin-1-yl)methanone
• CAS: 1361408-14-1
• 化学式: C₂₈H₃₃N₃O
• 分子量: 427.59
• InChiKey: KRJNMVCVRLHURT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,3,4,5-四氢-1H-吡啶并[4,3-b]吲哚-8-羧酸 在 三乙酰氧基硼氢化钠 、 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-) 、 三氟乙酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2-benzyl-5-prop-2-enyl-3,4-dihydro-1H-pyrido[4,3-b]indol-8-yl)-(4-methylpiperidin-1-yl)methanone
  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

• γ-Carbolines: A novel class of cannabinoid agonists with high aqueous solubility and restricted CNS penetration
  作者：Yun-Xing Cheng、Mehrnaz Pourashraf、Xuehong Luo、Sanjay Srivastava、Christopher Walpole、Dominic Salois、Stephane St-Onge、Kemal Payza、Etienne Lessard、Xiao Hong Yu、Mirosław J. Tomaszewski

  DOI：10.1016/j.bmcl.2011.12.124

  日期：2012.2

  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.