tert-butyl 1-(4-(3-bromopyrazolo[1,5-a]pyridin-2-yl)phenyl)cyclobutylcarbamate | 1357270-54-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: tert-butyl 1-(4-(3-bromopyrazolo[1,5-a]pyridin-2-yl)phenyl)cyclobutylcarbamate
• 英文别名: tert-butyl N-[1-[4-(3-bromopyrazolo[1,5-a]pyridin-2-yl)phenyl]cyclobutyl]carbamate
• CAS: 1357270-54-2
• 化学式: C₂₂H₂₄BrN₃O₂
• 分子量: 442.355
• InChiKey: LBIGPLBRCZLTGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 1-(4-(3-bromopyrazolo[1,5-a]pyridin-2-yl)phenyl)cyclobutylcarbamate 、 苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以60%的产率得到tert-butyl 1-(4-(3-phenylpyrazolo[1,5-a]pyridin-2-yl)phenyl)cyclobutylcarbamate
  参考文献：
  名称：

  Diverse Heterocyclic Scaffolds as Allosteric Inhibitors of AKT

  摘要：

  Wide-ranging exploration of potential replacements for a quinoline-based inhibitor of activation of AKT kinase led to number of alternative, novel scaffolds with potentially improved potency and physicochemical properties. Examples showed predictable DMPK properties, and one such compound demonstrated pharmacodynamic knockdown of phosphorylation of AKT and downstream biomarkers in vivo and inhibition of tumor growth in a breast cancer xenograft model.

  DOI：

  10.1021/jm201394e
• 作为产物：
  描述：

  ethyl 3-(4-(1-(tert-butoxycarbonyl(ethoxycarbonyl)amino)cyclobutyl)phenyl)propiolate 在 N-溴代丁二酰亚胺(NBS) 、 sodium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.5h， 生成 tert-butyl 1-(4-(3-bromopyrazolo[1,5-a]pyridin-2-yl)phenyl)cyclobutylcarbamate
  参考文献：
  名称：

  Diverse Heterocyclic Scaffolds as Allosteric Inhibitors of AKT

  摘要：

  Wide-ranging exploration of potential replacements for a quinoline-based inhibitor of activation of AKT kinase led to number of alternative, novel scaffolds with potentially improved potency and physicochemical properties. Examples showed predictable DMPK properties, and one such compound demonstrated pharmacodynamic knockdown of phosphorylation of AKT and downstream biomarkers in vivo and inhibition of tumor growth in a breast cancer xenograft model.

  DOI：

  10.1021/jm201394e

文献信息

• Diverse Heterocyclic Scaffolds as Allosteric Inhibitors of AKT
  作者：Jason G. Kettle、Simon Brown、Claire Crafter、Barry R. Davies、Phillippa Dudley、Gary Fairley、Paul Faulder、Shaun Fillery、Hannah Greenwood、Janet Hawkins、Michael James、Keith Johnson、Clare D. Lane、Martin Pass、Jennifer H. Pink、Helen Plant、Sabina C. Cosulich

  DOI：10.1021/jm201394e

  日期：2012.2.9

  Wide-ranging exploration of potential replacements for a quinoline-based inhibitor of activation of AKT kinase led to number of alternative, novel scaffolds with potentially improved potency and physicochemical properties. Examples showed predictable DMPK properties, and one such compound demonstrated pharmacodynamic knockdown of phosphorylation of AKT and downstream biomarkers in vivo and inhibition of tumor growth in a breast cancer xenograft model.