N-(adamantan-1-yl)-2-(5-phenyl-1H-indol-3-yl)acetamide | 1378020-86-0

• 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: N-(adamantan-1-yl)-2-(5-phenyl-1H-indol-3-yl)acetamide
• 英文别名: N-(1-adamantyl)-2-(5-phenyl-1H-indol-3-yl)acetamide
• CAS: 1378020-86-0
• 化学式: C₂₆H₂₈N₂O
• 分子量: 384.521
• InChiKey: BVSBLNRNBLBOSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  N-(adamantan-1-yl)-2-(5-phenyl-1H-indol-3-yl)acetamide 、 alkaline earth salt of/the/ methylsulfuric acid 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 以54%的产率得到N-(adamantan-1-yl)-2-(5-phenyl-1-propyl-1H-indol-3-yl)acetamide
  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：

  5-溴吲哚-3-乙酸 在 palladium diacetate 、 sodium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三苯基膦 作用下， 以 乙二醇二甲醚 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 2.17h， 生成 N-(adamantan-1-yl)-2-(5-phenyl-1H-indol-3-yl)acetamide
  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

文献信息

• Design, Synthesis, and Pharmacological Characterization of Indol-3-ylacetamides, Indol-3-yloxoacetamides, and Indol-3-ylcarboxamides: Potent and Selective CB2 Cannabinoid Receptor Inverse Agonists
  作者：Serena Pasquini、Claudia Mugnaini、Alessia Ligresti、Andrea Tafi、Simone Brogi、Chiara Falciani、Valentina Pedani、Nicolò Pesco、Francesca Guida、Livio Luongo、Katia Varani、Pier Andrea Borea、Sabatino Maione、Vincenzo Di Marzo、Federico Corelli

  DOI：10.1021/jm3003334

  日期：2012.6.14

  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.