3-{[6-[(2-hydroxyethyl)amino]-1-(2-phenylpropyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]amino}phenol

• 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: 3-{[6-[(2-hydroxyethyl)amino]-1-(2-phenylpropyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]amino}phenol
• 英文别名: 3-[[6-(2-Hydroxyethylamino)-1-(2-phenylpropyl)pyrazolo[3,4-d]pyrimidin-4-yl]amino]phenol；3-[[6-(2-hydroxyethylamino)-1-(2-phenylpropyl)pyrazolo[3,4-d]pyrimidin-4-yl]amino]phenol
• 化学式: C₂₂H₂₄N₆O₂
• 分子量: 404.472
• InChiKey: AHATUIZODRKCIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  108
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-{[6-(methylthio)-1-(2-phenylpropyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]amino}phenol 、 C.I.酸性橙108 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 、 正丁醇 为溶剂， 反应 9.0h， 以80%的产率得到3-{[6-[(2-hydroxyethyl)amino]-1-(2-phenylpropyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]amino}phenol
  参考文献：
  名称：

  Efficient optimization of pyrazolo[3,4-d]pyrimidines derivatives as c-Src kinase inhibitors in neuroblastoma treatment

  摘要：

  The proto-oncogene c-Src is a non-receptor tyrosine kinase which is involved in the regulation of many cellular processes, such as differentiation, adhesion and survival. c-Src hyperactivation has been detected in many tumors, including neuroblastoma (NB), one of the major causes of death from neoplasia in infancy. We already reported a large family of pyrazolo[3,4-d]pyrimidines active as c-Src inhibitors. Interestingly, some of these derivatives resulted also active on SH-SY5Y NB cell line. Herein, starting from our previous Free Energy Perturbation/Monte Carlo calculations, we report an optimization study which led to the identification of a new series of derivatives endowed with nanomolar K-i values against c-Src, interesting antiproliferative activity on SH-SY5Y cells and a suitable ADME profile.

  DOI：

  10.1016/j.bmcl.2018.09.024

文献信息

• Efficient optimization of pyrazolo[3,4-d]pyrimidines derivatives as c-Src kinase inhibitors in neuroblastoma treatment
  作者：Alessio Molinari、Anna Lucia Fallacara、Salvatore Di Maria、Claudio Zamperini、Federica Poggialini、Francesca Musumeci、Silvia Schenone、Adriano Angelucci、Alessandro Colapietro、Emmanuele Crespan、Miroslava Kissova、Giovanni Maga、Maurizio Botta

  DOI：10.1016/j.bmcl.2018.09.024

  日期：2018.11

  The proto-oncogene c-Src is a non-receptor tyrosine kinase which is involved in the regulation of many cellular processes, such as differentiation, adhesion and survival. c-Src hyperactivation has been detected in many tumors, including neuroblastoma (NB), one of the major causes of death from neoplasia in infancy. We already reported a large family of pyrazolo[3,4-d]pyrimidines active as c-Src inhibitors. Interestingly, some of these derivatives resulted also active on SH-SY5Y NB cell line. Herein, starting from our previous Free Energy Perturbation/Monte Carlo calculations, we report an optimization study which led to the identification of a new series of derivatives endowed with nanomolar K-i values against c-Src, interesting antiproliferative activity on SH-SY5Y cells and a suitable ADME profile.