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

• 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-aminoethyl)amino]-1-(2-phenylpropyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]amino}-4-chlorophenol
• 英文别名: 3-[[6-(2-Aminoethylamino)-1-(2-phenylpropyl)pyrazolo[3,4-d]pyrimidin-4-yl]amino]-4-chlorophenol；3-[[6-(2-aminoethylamino)-1-(2-phenylpropyl)pyrazolo[3,4-d]pyrimidin-4-yl]amino]-4-chlorophenol
• 化学式: C₂₂H₂₄ClN₇O
• 分子量: 437.932
• InChiKey: YPVYLNANXKPTGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 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：
  114
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-氯-3-硝基苯酚 在 铁粉 、 氯化铵 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 18.0h， 生成 3-{[6-[(2-aminoethyl)amino]-1-(2-phenylpropyl)-1H-pyrazolo[3,4-d]pyrimidin-4-yl]amino}-4-chlorophenol
  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.