3-[7-[(3-hydroxyphenyl)amino]pyrazolo[1,5-a]pyrimidin-2-yl]-N-(1-hydroxy-2,2,6,6-tetramethyl-piperidin-4-yl)benzamide | 1203705-51-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-[7-[(3-hydroxyphenyl)amino]pyrazolo[1,5-a]pyrimidin-2-yl]-N-(1-hydroxy-2,2,6,6-tetramethyl-piperidin-4-yl)benzamide
• 英文别名: 3-[7-(3-hydroxyanilino)pyrazolo[1,5-a]pyrimidin-2-yl]-N-(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl)benzamide
• CAS: 1203705-51-4
• 化学式: C₂₈H₃₂N₆O₃
• 分子量: 500.6
• InChiKey: WZEJOLDIQBJKQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  115
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-{7-[(3-hydroxyphenyl)amino]pyrazolo[1,5-α]pyrimidin-2-yl}-N-(1-oxy-2,2,6,6-tetramethylpiperidin-4-yl)benzamide 在 维生素 C 作用下， 以 氘代二甲亚砜 为溶剂， 生成 3-[7-[(3-hydroxyphenyl)amino]pyrazolo[1,5-a]pyrimidin-2-yl]-N-(1-hydroxy-2,2,6,6-tetramethyl-piperidin-4-yl)benzamide
  参考文献：
  名称：

  Novel Synthesis and Structural Characterization of a High-Affinity Paramagnetic Kinase Probe for the Identification of Non-ATP Site Binders by Nuclear Magnetic Resonance

  摘要：

  To aid in the pursuit of selective kinase inhibitors, we have developed a unique ATP site binder tool for the detection of binders outside the ATP site by nuclear magnetic resonance (NMR). We report here the novel synthesis that led to this paramagnetic spin-labeled pyrazolopyrimidine probe (1), which exhibits nanomolar inhibitory activity against multiple kinases. We demonstrate the application of this probe by performing NMR binding experiments with Lck and Src kinases and utilize it to detect the binding of two compounds proximal to the ATP site. The complex structure of the probe with Lck is also presented, revealing how the probe fits in the ATP site and the specific interactions it has with the protein. We believe that this spin-labeled probe is a valuable tool that holds broad applicability in a screen for non-ATP site binders.

  DOI：

  10.1021/jm901525b