(5-bromo-1H-indol-3-yl)-N-(adamantan-1-yl)carboxamide | 1378020-94-0

• 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: (5-bromo-1H-indol-3-yl)-N-(adamantan-1-yl)carboxamide
• 英文别名: N-(adamantan-1-yl)-5-bromo-1H-indole-3-carboxamide；N-(1-adamantyl)-5-bromo-1H-indole-3-carboxamide
• CAS: 1378020-94-0
• 化学式: C₁₉H₂₁BrN₂O
• 分子量: 373.293
• InChiKey: CQAVYVZGAAQWJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5-bromo-1H-indol-3-yl)-N-(adamantan-1-yl)carboxamide 在 四丁基溴化铵 、 palladium diacetate 、 sodium carbonate 、 三苯基膦 、 sodium hydroxide 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 0.17h， 生成 N-(adamantan-1-yl)-1-pentyl-5-(thiophen-2-yl)-1H-indole-3-carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Characterization of Indol-3-ylacetamides, Indol-3-yloxoacetamides, and Indol-3-ylcarboxamides: Potent and Selective CB2 Cannabinoid Receptor Inverse Agonists

  摘要：

  In our search for new cannabinoid receptor modulators, we describe herein the design and synthesis of three sets of indole-based ligands characterized by an acetamide, oxalylamide, or carboxamide chain, respectively. Most of the compounds showed affinity for CB2 receptors in the nanomolar range, with K-i values spanning 3 orders of magnitude (377-0.37 nM), and moderate to good selectivity over CB1 receptors. Their in vitro functional activity as inverse agonists was confirmed in vivo in the formalin test of acute peripheral and inflammatory pain in mice, in which compounds 10a and 11e proved to be able to reverse the effect of the CB2 selective agonist COR167.

  DOI：

  10.1021/jm3003334
• 作为产物：
  描述：

  金刚烷胺 、 5-溴-1H-吲哚-3-甲酸 在 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.75h， 以76%的产率得到(5-bromo-1H-indol-3-yl)-N-(adamantan-1-yl)carboxamide
  参考文献：
  名称：

  Design, Synthesis, and Pharmacological Characterization of Indol-3-ylacetamides, Indol-3-yloxoacetamides, and Indol-3-ylcarboxamides: Potent and Selective CB2 Cannabinoid Receptor Inverse Agonists

  摘要：

  In our search for new cannabinoid receptor modulators, we describe herein the design and synthesis of three sets of indole-based ligands characterized by an acetamide, oxalylamide, or carboxamide chain, respectively. Most of the compounds showed affinity for CB2 receptors in the nanomolar range, with K-i values spanning 3 orders of magnitude (377-0.37 nM), and moderate to good selectivity over CB1 receptors. Their in vitro functional activity as inverse agonists was confirmed in vivo in the formalin test of acute peripheral and inflammatory pain in mice, in which compounds 10a and 11e proved to be able to reverse the effect of the CB2 selective agonist COR167.

  DOI：

  10.1021/jm3003334