1-isopropyl-3-(3-methylbut-3-en-1-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine | 1379525-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 1-isopropyl-3-(3-methylbut-3-en-1-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
• 英文别名: 3-(3-Methylbut-3-en-1-ynyl)-1-propan-2-ylpyrazolo[3,4-d]pyrimidin-4-amine
• CAS: 1379525-81-1
• 化学式: C₁₃H₁₅N₅
• 分子量: 241.296
• InChiKey: UIJQSJMIUKIBRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-碘-4-氨基吡唑并[3,4-d]嘧啶 在 copper(l) iodide 、 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 生成 1-isopropyl-3-(3-methylbut-3-en-1-ynyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine
  参考文献：
  名称：

  Preparation of 3-Substituted-1-Isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amines as RET Kinase Inhibitors

  摘要：

  A series of 3-substituted-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amines have been designed, synthesized, and evaluated as RET protein kinase inhibitors. On the basis of docking results, a small library of pyrazolopyrimidine compounds with an extended hydrophobic side arm was synthesized. The most promising of the compounds (7a) displayed efficient inhibition in vitro and good selectivity when tested on a panel of kinases. Furthermore, 7a inhibited GDNF-induced RET phosphorylation of ERK1/2 in MCF-7 breast cancer cells at concentrations as low as 100 nM.

  DOI：

  10.1021/jm3003944

文献信息

• Preparation of 3-Substituted-1-Isopropyl-1<i>H</i>-pyrazolo[3,4-<i>d</i>]pyrimidin-4-amines as RET Kinase Inhibitors
  作者：Peter Dinér、John P. Alao、Johan Söderlund、Per Sunnerhagen、Morten Grøtli

  DOI：10.1021/jm3003944

  日期：2012.5.24

  A series of 3-substituted-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amines have been designed, synthesized, and evaluated as RET protein kinase inhibitors. On the basis of docking results, a small library of pyrazolopyrimidine compounds with an extended hydrophobic side arm was synthesized. The most promising of the compounds (7a) displayed efficient inhibition in vitro and good selectivity when tested on a panel of kinases. Furthermore, 7a inhibited GDNF-induced RET phosphorylation of ERK1/2 in MCF-7 breast cancer cells at concentrations as low as 100 nM.