diethyl (5-{[6-(2-methoxyphenyl)pyrimidin-4-yl]amino}-2-methylbenzyl)phosphonate | 1606168-71-1

• 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: diethyl (5-{[6-(2-methoxyphenyl)pyrimidin-4-yl]amino}-2-methylbenzyl)phosphonate
• 英文别名: N-[3-(diethoxyphosphorylmethyl)-4-methyl-phenyl]-6-(2-methoxyphenyl)pyrimidin-4-amine；N-[3-(diethoxyphosphorylmethyl)-4-methylphenyl]-6-(2-methoxyphenyl)pyrimidin-4-amine
• CAS: 1606168-71-1
• 化学式: C₂₃H₂₈N₃O₄P
• 分子量: 441.467
• InChiKey: OUSKEGTXGKODAX-UHFFFAOYSA-N

物化性质

• 熔点：
  134-137 °C(Solvent: Methanol)
• 沸点：
  596.617±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.204±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  82.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-甲基-5-硝基苯甲酸 在 盐酸 、 lithium aluminium tetrahydride 、 硫酸 、 palladium 10% on activated carbon 、 甲酸铵 、 三溴化磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醇 、 水 为溶剂， 反应 48.17h， 生成 diethyl (5-{[6-(2-methoxyphenyl)pyrimidin-4-yl]amino}-2-methylbenzyl)phosphonate
  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.