1-ethyl-4-pyrrolidin-1-yl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester | 34966-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: 1-ethyl-4-pyrrolidin-1-yl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester
• 英文别名: Ethyl 1-ethyl-4-pyrrolidin-1-ylpyrazolo[3,4-b]pyridine-5-carboxylate
• CAS: 34966-44-4
• 化学式: C₁₅H₂₀N₄O₂
• 分子量: 288.349
• InChiKey: QGABASIWTCMUEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 4-氯-1-乙基-1H-吡唑[3,4-b]吡啶-5-羧酸乙酯 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 1-ethyl-4-pyrrolidin-1-yl-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  Pyrazolopyridines as a novel structural class of potent and selective PDE4 inhibitors

  摘要：

  Optimisation of a high-throughput screening hit resulted in the discovery of 4-(substituted amino)-1-alkyl-pyrazolo[3,4-b]pyridine-5-carboxamides as potent and selective inhibitors of Phosphodiesterase 4 (PDE4). Herein, we describe early SAR studies around this novel template highlighting preferred substituents and rationalization of SAR through X-ray crystal structures of analogues bound to the PDE4 active site. Pyrazolopyridine 20a was found to be a potent and selective PDE4 inhibitor which also inhibits LPS induced TNF-alpha production from isolated human peripheral blood mononuclear cells and has an encouraging rat PK profile suitable for oral dosing.

  DOI：

  10.1016/j.bmcl.2008.05.052

文献信息

• Pyrazolopyridines as a novel structural class of potent and selective PDE4 inhibitors
  作者：J. Nicole Hamblin、Tony D.R. Angell、Stuart P. Ballantine、Caroline M. Cook、Anthony W.J. Cooper、John Dawson、Christopher J. Delves、Paul S. Jones、Mika Lindvall、Fiona S. Lucas、Charlotte J. Mitchell、Margarete Y. Neu、Lisa E. Ranshaw、Yemisi E. Solanke、Don O. Somers、Joanne O. Wiseman

  DOI：10.1016/j.bmcl.2008.05.052

  日期：2008.7

  Optimisation of a high-throughput screening hit resulted in the discovery of 4-(substituted amino)-1-alkyl-pyrazolo[3,4-b]pyridine-5-carboxamides as potent and selective inhibitors of Phosphodiesterase 4 (PDE4). Herein, we describe early SAR studies around this novel template highlighting preferred substituents and rationalization of SAR through X-ray crystal structures of analogues bound to the PDE4 active site. Pyrazolopyridine 20a was found to be a potent and selective PDE4 inhibitor which also inhibits LPS induced TNF-alpha production from isolated human peripheral blood mononuclear cells and has an encouraging rat PK profile suitable for oral dosing.