[5-methoxy-2-methyl-1-(1-benzyl-piperidin-4-yl)-1H-indol-3-yl]-acetic acid | 1184873-10-6

• 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: [5-methoxy-2-methyl-1-(1-benzyl-piperidin-4-yl)-1H-indol-3-yl]-acetic acid
• 英文别名: 2-(1-(1-Benzylpiperidin-4-YL)-5-methoxy-2-methyl-1H-indol-3-YL)acetic acid；2-[1-(1-benzylpiperidin-4-yl)-5-methoxy-2-methylindol-3-yl]acetic acid
• CAS: 1184873-10-6
• 化学式: C₂₄H₂₈N₂O₃
• 分子量: 392.498
• InChiKey: GNCCHLCPNRXYPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 盐酸 作用下， 以 乙醇 为溶剂， 生成 [5-methoxy-2-methyl-1-(1-benzyl-piperidin-4-yl)-1H-indol-3-yl]-acetic acid
  参考文献：
  名称：

  Synthesis and investigations of double-pharmacophore ligands for treatment of chronic and neuropathic pain

  摘要：

  Acids 9a-f as possible bivalent ligands designed as a structural combination of opioid mu-agonist (Fentanyl) and NSAID ( Indomethacin) activities and produced compounds which were tested as analgesics. The obtained series of compounds exhibits low affinity and activity both at opioid receptors and as cyclooxygenase ( COX) inhibitors. One explanation of the weak opioid activity could be stereochemical peculiarities of these bivalent compounds which differ significantly from the fentanyl skeleton. The absence of significant COX inhibitory properties could be explained by the required substitution of an acyl fragment in the indomethacin structure for 4-piperidyl. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2009.05.065

文献信息

• Synthesis and investigations of double-pharmacophore ligands for treatment of chronic and neuropathic pain
  作者：Ruben Vardanyan、Gokhale Vijay、Gary S. Nichol、Lu Liu、Isuru Kumarasinghe、Peg Davis、Todd Vanderah、Frank Porreca、Josephine Lai、Victor J. Hruby

  DOI：10.1016/j.bmc.2009.05.065

  日期：2009.7

  Acids 9a-f as possible bivalent ligands designed as a structural combination of opioid mu-agonist (Fentanyl) and NSAID ( Indomethacin) activities and produced compounds which were tested as analgesics. The obtained series of compounds exhibits low affinity and activity both at opioid receptors and as cyclooxygenase ( COX) inhibitors. One explanation of the weak opioid activity could be stereochemical peculiarities of these bivalent compounds which differ significantly from the fentanyl skeleton. The absence of significant COX inhibitory properties could be explained by the required substitution of an acyl fragment in the indomethacin structure for 4-piperidyl. Published by Elsevier Ltd.