4-(4-amino-3-(4-((7-chlorobenzo[d]oxazol-2-yl)amino)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexan-1-one | 1253107-49-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-amino-3-(4-((7-chlorobenzo[d]oxazol-2-yl)amino)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexan-1-one
• CAS: 1253107-49-1
• 化学式: C₂₄H₂₀ClN₇O₂
• 分子量: 473.922
• InChiKey: NIVUMDZMDMOVGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  124.75
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-(4-amino-3-(4-((7-chlorobenzo[d]oxazol-2-yl)amino)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexan-1-one 、 1-(2-吡啶-2-基乙基)哌嗪 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 2-(4-((1r,4r)-4-(4-amino-3-(4-((7-chlorobenzo[d]oxazol-2-yl)amino)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexyl)piperazin-1-yl)-N,N-dimethylacetamide
  参考文献：
  名称：

  Substituted 4-amino-1H-pyrazolo[3,4-d]pyrimidines as multi-targeted inhibitors of insulin-like growth factor-1 receptor (IGF1R) and members of ErbB-family receptor kinases

  摘要：

  This Letter describes the lead discovery, optimization, and biological characterization of a series of substituted 4-amino-1H-pyrazolo[3,4-d]pyrimidines as potent inhibitors of IGF1R, EGFR, and ErbB2. The leading compound 11 showed an IGF1R IC50 of 12 nM, an EGFR (L858R) IC50 of 31 nM, and an ErbB2 IC50 of 11 nM, potent activity in cellular functional and anti-proliferation assays, as well as activity in an in vivo pharmacodynamic assay. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.052
• 作为产物：
  描述：

  7-chloro-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]oxazol-2-amine 、 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexanone 在 四(三苯基膦)钯 、 cesium fluoride 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 以56%的产率得到4-(4-amino-3-(4-((7-chlorobenzo[d]oxazol-2-yl)amino)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)cyclohexan-1-one
  参考文献：
  名称：

  Substituted 4-amino-1H-pyrazolo[3,4-d]pyrimidines as multi-targeted inhibitors of insulin-like growth factor-1 receptor (IGF1R) and members of ErbB-family receptor kinases

  摘要：

  This Letter describes the lead discovery, optimization, and biological characterization of a series of substituted 4-amino-1H-pyrazolo[3,4-d]pyrimidines as potent inhibitors of IGF1R, EGFR, and ErbB2. The leading compound 11 showed an IGF1R IC50 of 12 nM, an EGFR (L858R) IC50 of 31 nM, and an ErbB2 IC50 of 11 nM, potent activity in cellular functional and anti-proliferation assays, as well as activity in an in vivo pharmacodynamic assay. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.052