ethyl [3-({6-[2-(benzyloxy)phenyl]pyrimidin-4-yl}amino)benzyl]ethylphosphinate | 1606169-42-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ethyl [3-({6-[2-(benzyloxy)phenyl]pyrimidin-4-yl}amino)benzyl]ethylphosphinate
• 英文别名: 6-(2-benzyloxyphenyl)-N-[3-[[ethoxy(ethyl)phosphoryl]methyl]phenyl]pyrimidin-4-amine；N-[3-[[ethoxy(ethyl)phosphoryl]methyl]phenyl]-6-(2-phenylmethoxyphenyl)pyrimidin-4-amine
• CAS: 1606169-42-9
• 化学式: C₂₈H₃₀N₃O₃P
• 分子量: 487.538
• InChiKey: LDLGEHYWPPYLOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  73.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl [3-({6-[2-(benzyloxy)phenyl]pyrimidin-4-yl}amino)benzyl]ethylphosphinate 在 三甲基氯硅烷 、 potassium iodide 作用下， 以 氯仿 为溶剂， 反应 44.0h， 以19%的产率得到[3-({6-[2-(benzyloxy)phenyl]pyrimidin-4-yl}amino)benzyl]ethylphosphinic acid
  参考文献：
  名称：

  Synthesis and Evaluation of Phosphorus Containing, Specific CDK9/CycT1 Inhibitors

  摘要：

  Although there is a significant effort in the design of a selective CDK9/CycT1 inhibitor, no compound has been proven to be a specific inhibitor of this kinase so far. The aim of this research was to develop novel and selective phosphorus containing CDK9/CycT1 inhibitors. Molecules bearing phosphonamidate, phosphonate, and phosphinate moieties were synthesized. Prepared compounds were evaluated in an enzymatic CDK9/CycT1 assay. The most potent molecules were tested in cell-based toxicity and HIV proliferation assays. Selectivity of shortlisted compounds against CDKs and other kinases was tested. The best compound was shown to be a highly specific, ATP-competitive inhibitor of CDK9/CycT1 with antiviral activity.

  DOI：

  10.1021/jm401742r
• 作为产物：
  描述：

  2-苄氧基苯硼酸 在 盐酸 、 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 、 乙二醇二甲醚 、 乙醇 、 水 为溶剂， 反应 21.5h， 生成 ethyl [3-({6-[2-(benzyloxy)phenyl]pyrimidin-4-yl}amino)benzyl]ethylphosphinate
  参考文献：
  名称：

  Synthesis and Evaluation of Phosphorus Containing, Specific CDK9/CycT1 Inhibitors

  摘要：

  Although there is a significant effort in the design of a selective CDK9/CycT1 inhibitor, no compound has been proven to be a specific inhibitor of this kinase so far. The aim of this research was to develop novel and selective phosphorus containing CDK9/CycT1 inhibitors. Molecules bearing phosphonamidate, phosphonate, and phosphinate moieties were synthesized. Prepared compounds were evaluated in an enzymatic CDK9/CycT1 assay. The most potent molecules were tested in cell-based toxicity and HIV proliferation assays. Selectivity of shortlisted compounds against CDKs and other kinases was tested. The best compound was shown to be a highly specific, ATP-competitive inhibitor of CDK9/CycT1 with antiviral activity.

  DOI：

  10.1021/jm401742r

文献信息

• Synthesis and Evaluation of Phosphorus Containing, Specific CDK9/CycT1 Inhibitors
  作者：Gábor Németh、Zoltán Greff、Anna Sipos、Zoltán Varga、Rita Székely、Mónika Sebestyén、Zsuzsa Jászay、Szabolcs Béni、Zoltán Nemes、Jean-Luc Pirat、Jean-Noël Volle、David Virieux、Ágnes Gyuris、Katalin Kelemenics、Éva Áy、Janos Minarovits、Susan Szathmary、György Kéri、László Őrfi

  DOI：10.1021/jm401742r

  日期：2014.5.22

  Although there is a significant effort in the design of a selective CDK9/CycT1 inhibitor, no compound has been proven to be a specific inhibitor of this kinase so far. The aim of this research was to develop novel and selective phosphorus containing CDK9/CycT1 inhibitors. Molecules bearing phosphonamidate, phosphonate, and phosphinate moieties were synthesized. Prepared compounds were evaluated in an enzymatic CDK9/CycT1 assay. The most potent molecules were tested in cell-based toxicity and HIV proliferation assays. Selectivity of shortlisted compounds against CDKs and other kinases was tested. The best compound was shown to be a highly specific, ATP-competitive inhibitor of CDK9/CycT1 with antiviral activity.