1-[[5-[1-Ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3,4-oxadiazol-2-yl]methyl]pyrrolidin-2-one | 1253583-60-6

• 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-[[5-[1-Ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3,4-oxadiazol-2-yl]methyl]pyrrolidin-2-one
• CAS: 1253583-60-6
• 化学式: C₂₀H₂₅N₇O₃
• 分子量: 411.464
• InChiKey: JXISUDUMXDDGNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  、 4-氯丁酰氯 在 N,N-二异丙基乙胺 、 sodium hydride 作用下， 以 乙腈 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以43%的产率得到1-[[5-[1-Ethyl-4-(oxan-4-ylamino)pyrazolo[3,4-b]pyridin-5-yl]-1,3,4-oxadiazol-2-yl]methyl]pyrrolidin-2-one
  参考文献：
  名称：

  Pyrazolopyridines as potent PDE4B inhibitors: 5-Heterocycle SAR

  摘要：

  Following the discovery of 4-(substituted amino)-1-alkyl-pyrazolo[3,4-b]pyridine-5-carboxamides as potent and selective phosphodiesterase 4B inhibitors, [Hamblin, J. N.; Angell, T.; Ballentine, S., et al. Bioorg. Med. Chem. Lett. 2008, 18, 4237] the SAR of the 5-position was investigated further. A range of substituted heterocycles showed good potencies against PDE4. Optimisation using X-ray crystallography and computational modelling led to the discovery of 16, with sub-nM inhibition of LPS-induced TNF-alpha production from isolated human peripheral blood mononuclear cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.136

文献信息

• Pyrazolopyridines as potent PDE4B inhibitors: 5-Heterocycle SAR
  作者：Charlotte J. Mitchell、Stuart P. Ballantine、Diane M. Coe、Caroline M. Cook、Christopher J. Delves、Mike D. Dowle、Chris D. Edlin、J. Nicole Hamblin、Stuart Holman、Martin R. Johnson、Paul S. Jones、Sue E. Keeling、Michael Kranz、Mika Lindvall、Fiona S. Lucas、Margarete Neu、Yemisi E. Solanke、Don O. Somers、Naimisha A. Trivedi、Joanne O. Wiseman

  DOI：10.1016/j.bmcl.2010.07.136

  日期：2010.10

  Following the discovery of 4-(substituted amino)-1-alkyl-pyrazolo[3,4-b]pyridine-5-carboxamides as potent and selective phosphodiesterase 4B inhibitors, [Hamblin, J. N.; Angell, T.; Ballentine, S., et al. Bioorg. Med. Chem. Lett. 2008, 18, 4237] the SAR of the 5-position was investigated further. A range of substituted heterocycles showed good potencies against PDE4. Optimisation using X-ray crystallography and computational modelling led to the discovery of 16, with sub-nM inhibition of LPS-induced TNF-alpha production from isolated human peripheral blood mononuclear cells. (C) 2010 Elsevier Ltd. All rights reserved.