tert-butyl 2'-(2-chloropyridin-4-yl)-4'-oxo-1',4',5',6'-tetrahydrospiro[pyrrolidine-3,7'-pyrrolo[3,2-c]pyridine]-1-carboxylate | 1354531-79-5

• 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: tert-butyl 2'-(2-chloropyridin-4-yl)-4'-oxo-1',4',5',6'-tetrahydrospiro[pyrrolidine-3,7'-pyrrolo[3,2-c]pyridine]-1-carboxylate
• CAS: 1354531-79-5
• 化学式: C₂₀H₂₃ClN₄O₃
• 分子量: 402.881
• InChiKey: FSTZWZHEZJLETE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.35
• 重原子数：
  28.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  87.32
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2'-(2-chloropyridin-4-yl)-4'-oxo-1',4',5',6'-tetrahydrospiro[pyrrolidine-3,7'-pyrrolo[3,2-c]pyridine]-1-carboxylate 在 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene 、 palladium diacetate 、 三氟乙酸 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-(4-(4'-oxo-1',4',5',6'-tetrahydrospiro[pyrrolidine-3,7'-pyrrolo[3,2-c]pyridine]-2'yl)pyridin-2-yl)-3-(trifluoromethoxy)benzamide
  参考文献：
  名称：

  Novel ATP competitive MK2 inhibitors with potent biochemical and cell-based activity throughout the series

  摘要：

  Optimization of our previously described pyrrolopiperidone series led to the identification of a new benzamide sub-series, which exhibits consistently high potency in biochemical and cell-based assays throughout the series. Strong inhibition of LPS-induced production of the cytokine TNF alpha is coupled to the regulation of HSP27 phosphorylation, indicating that the observed cellular effects result from the inhibition of MK2. X-ray crystallographic and computational analyses provide a rationale for the high potency of the series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.071
• 作为产物：
  描述：

  在 ammonium acetate 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 生成 tert-butyl 2'-(2-chloropyridin-4-yl)-4'-oxo-1',4',5',6'-tetrahydrospiro[pyrrolidine-3,7'-pyrrolo[3,2-c]pyridine]-1-carboxylate
  参考文献：
  名称：

  Novel ATP competitive MK2 inhibitors with potent biochemical and cell-based activity throughout the series

  摘要：

  Optimization of our previously described pyrrolopiperidone series led to the identification of a new benzamide sub-series, which exhibits consistently high potency in biochemical and cell-based assays throughout the series. Strong inhibition of LPS-induced production of the cytokine TNF alpha is coupled to the regulation of HSP27 phosphorylation, indicating that the observed cellular effects result from the inhibition of MK2. X-ray crystallographic and computational analyses provide a rationale for the high potency of the series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.10.071