Imidazo[1,5-a]pyrazine-3-carboxylic acid,1-(4-morpholinyl)-,ethyl ester | 1304065-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并[1,5-a]吡嗪
• 英文名称: Imidazo[1,5-a]pyrazine-3-carboxylic acid,1-(4-morpholinyl)-,ethyl ester
• 英文别名: ethyl 1-morpholin-4-ylimidazo[1,5-a]pyrazine-3-carboxylate
• CAS: 1304065-01-7
• 化学式: C₁₃H₁₆N₄O₃
• 分子量: 276.295
• InChiKey: FQMYXFPEBSMKMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  69
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Imidazo[1,5-a]pyrazine-3-carboxylic acid,1-(4-morpholinyl)-,ethyl ester 在 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-1-morpholino-N-(2,2,2-trifluoro-1-(pyridin-2-yl)ethyl)imidazo[1,5-a]pyrazine-3-carboxamide
  参考文献：
  名称：

  Imidazopyridine CB2 agonists: Optimization of CB2/CB1 selectivity and implications for in vivo analgesic efficacy

  摘要：

  A new series of imidazopyridine CB2 agonists is described. Structural optimization improved CB2/CB1 selectivity in this series and conferred physical properties that facilitated high in vivo exposure, both centrally and peripherally. Administration of a highly selective CB2 agonist in a rat model of analgesia was ineffective despite substantial CNS exposure, while administration of a moderately selective CB2/CB1 agonist exhibited significant analgesic effects. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.082
• 作为产物：
  描述：

  3-Carbethoxyimidazo<1,5-a>pyrazin 在 tris-(dibenzylideneacetone)dipalladium(0) 、 N-溴代丁二酰亚胺(NBS) 、 caesium carbonate 、 三乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 乙腈 为溶剂， 生成 Imidazo[1,5-a]pyrazine-3-carboxylic acid,1-(4-morpholinyl)-,ethyl ester
  参考文献：
  名称：

  Imidazopyridine CB2 agonists: Optimization of CB2/CB1 selectivity and implications for in vivo analgesic efficacy

  摘要：

  A new series of imidazopyridine CB2 agonists is described. Structural optimization improved CB2/CB1 selectivity in this series and conferred physical properties that facilitated high in vivo exposure, both centrally and peripherally. Administration of a highly selective CB2 agonist in a rat model of analgesia was ineffective despite substantial CNS exposure, while administration of a moderately selective CB2/CB1 agonist exhibited significant analgesic effects. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.082

文献信息

• Imidazopyridine CB2 agonists: Optimization of CB2/CB1 selectivity and implications for in vivo analgesic efficacy
  作者：B. Wesley Trotter、Kausik K. Nanda、Christopher S. Burgey、Craig M. Potteiger、James Z. Deng、Ahren I. Green、John C. Hartnett、Nathan R. Kett、Zhicai Wu、Darrell A. Henze、Kimberly Della Penna、Reshma Desai、Michael D. Leitl、Wei Lemaire、Rebecca B. White、Suzie Yeh、Mark O. Urban、Stefanie A. Kane、George D. Hartman、Mark T. Bilodeau

  DOI：10.1016/j.bmcl.2011.02.082

  日期：2011.4

  A new series of imidazopyridine CB2 agonists is described. Structural optimization improved CB2/CB1 selectivity in this series and conferred physical properties that facilitated high in vivo exposure, both centrally and peripherally. Administration of a highly selective CB2 agonist in a rat model of analgesia was ineffective despite substantial CNS exposure, while administration of a moderately selective CB2/CB1 agonist exhibited significant analgesic effects. (C) 2011 Elsevier Ltd. All rights reserved.