8-[3-Chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carbonyl]-2-ethyl-4-oxa-2,8-diazaspiro[4.5]decan-3-one | 1609198-57-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 英文名称: 8-[3-Chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carbonyl]-2-ethyl-4-oxa-2,8-diazaspiro[4.5]decan-3-one
• 英文别名: 8-[3-chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carbonyl]-3-ethyl-1-oxa-3,8-diazaspiro[4.5]decan-2-one
• CAS: 1609198-57-3
• 化学式: C₂₁H₂₂ClF₃N₄O₃
• 分子量: 470.879
• InChiKey: QVDFETCTOBMFLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-氧-3,8-二氮杂螺[4,5]癸烷-2-酮 在 sodium hydride 、 1-丙基磷酸酐 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 8-[3-Chloro-5-cyclopropyl-7-(trifluoromethyl)pyrazolo[1,5-a]pyridine-2-carbonyl]-2-ethyl-4-oxa-2,8-diazaspiro[4.5]decan-3-one
  参考文献：
  名称：

  Design and synthesis of spirocyclic compounds as HCV replication inhibitors by targeting viral NS4B protein

  摘要：

  Two novel series of spirocyclic piperidine analogs appended to a pyrazolo[1,5-alpha] pyridine core were designed, synthesized and evaluated for their anti-HCV activity. A series of piperidine ketals afforded dispiro 6p which showed excellent in vitro anti-HCV activities (EC50 of 1.5 nM and 1.2 nM against genotype 1a and 1b replicons, respectively). A series of piperidine oxazolidinones afforded 27c which showed EC50's of 10.9 nM and 6.1 nM against 1a and 1b replicons, respectively. Both compounds 6p and 27c bound directly to non-structural NS4B protein in vitro (IC50's = 10.2 and 30.4 nM, respectively) and exhibited reduced potency in replicons containing resistance mutations encoding changes in the NS4B protein. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.080