N-3-pentyl-4-(4-morpholinylcarbonyl)-1H-pyrrolo[2,3-c]pyridin-7-amine | 1189396-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: N-3-pentyl-4-(4-morpholinylcarbonyl)-1H-pyrrolo[2,3-c]pyridin-7-amine
• 英文别名: [3-methyl-7-(pentan-3-ylamino)-1H-pyrrolo[2,3-c]pyridin-4-yl]-morpholin-4-ylmethanone
• CAS: 1189396-20-0
• 化学式: C₁₈H₂₆N₄O₂
• 分子量: 330.43
• InChiKey: HXMNQTSLKJZKIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  70.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-3-pentyl-4-(4-morpholinylcarbonyl)-1H-pyrrolo[2,3-c]pyridin-7-amine 在 盐酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以19 mg的产率得到N-3-pentyl-4-(4-morpholinylcarbonyl)-1H-pyrrolo[2,3-c]pyridin-7-amine hydrochloride
  参考文献：
  名称：

  Discovery of 1-[4-(3-Chlorophenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-7-yl]-1-morpholin-4-ylmethanone (GSK554418A), a Brain Penetrant 5-Azaindole CB₂ Agonist for the Treatment of Chronic Pain

  摘要：

  We report the synthesis and SAR of a series of novel azaindole CB2 agonists. 6-Azaindole 18 showed activity in an acute pain model but was inactive in a chronic model. 18 is a Pgp substrate with low brain penetration. The template was redesigned, and the resulting 5-azaindole 36 was a potent CB2 agonist with high CNS penetration. This compound was efficacious in the acute model and the chronic joint pain model.

  DOI：

  10.1021/jm9009857
• 作为产物：
  描述：

  7-chloro-3-methyl-4-(1-morpholin-4-yl-methanoyl)-pyrrolo[2,3-c]pyridine-1-carboxylic acid tert-butyl ester 、 3-氨基戊烷 在 甲烷磺酸 、 N-甲基吡咯烷酮 作用下， 以 1,4-二氧六环 为溶剂， 反应 17.0h， 生成 N-3-pentyl-4-(4-morpholinylcarbonyl)-1H-pyrrolo[2,3-c]pyridin-7-amine
  参考文献：
  名称：

  Discovery of 1-[4-(3-Chlorophenylamino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-7-yl]-1-morpholin-4-ylmethanone (GSK554418A), a Brain Penetrant 5-Azaindole CB₂ Agonist for the Treatment of Chronic Pain

  摘要：

  We report the synthesis and SAR of a series of novel azaindole CB2 agonists. 6-Azaindole 18 showed activity in an acute pain model but was inactive in a chronic model. 18 is a Pgp substrate with low brain penetration. The template was redesigned, and the resulting 5-azaindole 36 was a potent CB2 agonist with high CNS penetration. This compound was efficacious in the acute model and the chronic joint pain model.

  DOI：

  10.1021/jm9009857

文献信息

• Discovery of 1-[4-(3-Chlorophenylamino)-1-methyl-1<i>H</i>-pyrrolo[3,2-<i>c</i>]pyridin-7-yl]-1-morpholin-4-ylmethanone (GSK554418A), a Brain Penetrant 5-Azaindole CB₂ Agonist for the Treatment of Chronic Pain
  作者：Gerard M. P. Giblin、Andrew Billinton、Michael Briggs、Andrew J. Brown、Iain P. Chessell、Nick M. Clayton、Andrew J. Eatherton、Paul Goldsmith、Carl Haslam、Matthew R. Johnson、William L. Mitchell、Alan Naylor、Alcide Perboni、Brian P. Slingsby、Alex W. Wilson

  DOI：10.1021/jm9009857

  日期：2009.10.8

  We report the synthesis and SAR of a series of novel azaindole CB2 agonists. 6-Azaindole 18 showed activity in an acute pain model but was inactive in a chronic model. 18 is a Pgp substrate with low brain penetration. The template was redesigned, and the resulting 5-azaindole 36 was a potent CB2 agonist with high CNS penetration. This compound was efficacious in the acute model and the chronic joint pain model.