N-[4-(4-oxospiro[5,6-dihydro-1H-pyrrolo[3,2-c]pyridine-7,4'-piperidine]-2-yl)pyridin-2-yl]-3-(trifluoromethoxy)benzamide | 1354531-07-9

• 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-[4-(4-oxospiro[5,6-dihydro-1H-pyrrolo[3,2-c]pyridine-7,4'-piperidine]-2-yl)pyridin-2-yl]-3-(trifluoromethoxy)benzamide
• CAS: 1354531-07-9
• 化学式: C₂₄H₂₂F₃N₅O₃
• 分子量: 485.466
• InChiKey: IYTUIXSZTJRKJK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N-[4-(4-oxospiro[5,6-dihydro-1H-pyrrolo[3,2-c]pyridine-7,4'-piperidine]-2-yl)pyridin-2-yl]-3-(trifluoromethoxy)benzamide 在 sodium cyanoborohydride 作用下， 以 乙腈 为溶剂， 反应 15.0h， 生成 N-(4-(1-methyl-4'-oxo-1',4',5',6'-tetrahydrospiro[piperidine-4,7'-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：

  1-(2-氯吡啶基)-2-溴乙酮 在 4,5-bis(diphenylphosphono)-9,9-dimethylxanthene 、 ammonium acetate 、 palladium diacetate 、 三氟乙酸 、 sodium t-butanolate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[4-(4-oxospiro[5,6-dihydro-1H-pyrrolo[3,2-c]pyridine-7,4'-piperidine]-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