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

文献信息

• Bone-Targeted Src kinase inhibitors: novel pyrrolo- and pyrazolopyrimidine analogues
  作者：Raji Sundaramoorthi、William C. Shakespeare、Terence P. Keenan、Chester A. Metcalf、Yihan Wang、Ukti Mani、Merry Taylor、Shuangying Liu、Regine S. Bohacek、Surinder S. Narula、David C. Dalgarno、Marie Rose Van Schravandijk、Sheila M. Violette、Shuenn Liou、Susan Adams、Mary K. Ram、Jeffrey A. Keats、Manfred Weigele、Tomi K. Sawyer

  DOI：10.1016/s0960-894x(03)00647-4

  日期：2003.9

  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.