3-[4-Amino-7-(4-{2-[(2-hydroxy-ethyl)-methyl-amino]-ethyl}-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-phenol | 344891-49-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-[4-Amino-7-(4-{2-[(2-hydroxy-ethyl)-methyl-amino]-ethyl}-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-phenol
• 英文别名: 3-[4-amino-7-[4-[2-[2-hydroxyethyl(methyl)amino]ethyl]phenyl]pyrrolo[2,3-d]pyrimidin-5-yl]phenol
• CAS: 344891-49-2
• 化学式: C₂₃H₂₅N₅O₂
• 分子量: 403.484
• InChiKey: LRSZQKQTVQFILF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  100
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-[4-Amino-7-(4-{2-[(2-hydroxy-ethyl)-methyl-amino]-ethyl}-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-phenol 在 磷酸三甲酯 、 水 作用下， 生成 ({2-[(2-{4-[4-Amino-5-(3-hydroxy-phenyl)-pyrrolo[2,3-d]pyrimidin-7-yl]-phenyl}-ethyl)-methyl-amino]-ethoxy}-hydroxy-phosphorylmethyl)-phosphonic acid
  参考文献：
  名称：

  Bone-Targeted Src kinase inhibitors: novel pyrrolo- and pyrazolopyrimidine analogues

  摘要：

  Src tyrosine kinase is a therapeutic target for bone diseases that has been validated by gene knockout studies. Furthermore, in vitro cellular studies implicate that Src has a positive regulatory role in osteoclasts and a negative regulatory role in osteoblasts. The potential use of Src inhibitors for osteoporosis therapy has been previously shown by novel bone-targeted ligands of the Src SH2 (e.g., AP22408) and non-bone-targeted, ATP-based inhibitors of Src kinase. Significant to this study, compounds 212 exemplify novel analogues of known pyrrolopyrimidine and pyrazolopyrimidine template-based Src kinase inhibitors that incorporate bone-targeting group modifications designed to provide tissue (bone) selectivity and diminished side effects. Accordingly, we report here the structure-based design, synthetic chemistry and biological testing of these compounds and proof-of-concept studies thereof. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00647-4
• 作为产物：
  描述：

  2-((4-(4-amino-5-(3-methoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)phenethyl)(methyl)amino)ethanol 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-[4-Amino-7-(4-{2-[(2-hydroxy-ethyl)-methyl-amino]-ethyl}-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-phenol
  参考文献：
  名称：

  Bone-Targeted Src kinase inhibitors: novel pyrrolo- and pyrazolopyrimidine analogues

  摘要：

  Src tyrosine kinase is a therapeutic target for bone diseases that has been validated by gene knockout studies. Furthermore, in vitro cellular studies implicate that Src has a positive regulatory role in osteoclasts and a negative regulatory role in osteoblasts. The potential use of Src inhibitors for osteoporosis therapy has been previously shown by novel bone-targeted ligands of the Src SH2 (e.g., AP22408) and non-bone-targeted, ATP-based inhibitors of Src kinase. Significant to this study, compounds 212 exemplify novel analogues of known pyrrolopyrimidine and pyrazolopyrimidine template-based Src kinase inhibitors that incorporate bone-targeting group modifications designed to provide tissue (bone) selectivity and diminished side effects. Accordingly, we report here the structure-based design, synthetic chemistry and biological testing of these compounds and proof-of-concept studies thereof. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00647-4