N-acetyl-O-[bis(benzyloxy)phosphoryl]-N'-{1-[2-(2-oxotetrahydropyrimidin-1(2H)-yl)ethyl]cyclohexyl}-L-tyrosinamide | 1268157-70-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-acetyl-O-[bis(benzyloxy)phosphoryl]-N'-{1-[2-(2-oxotetrahydropyrimidin-1(2H)-yl)ethyl]cyclohexyl}-L-tyrosinamide
• 英文别名: [4-[(2S)-2-acetamido-3-oxo-3-[[1-[2-(2-oxo-1,3-diazinan-1-yl)ethyl]cyclohexyl]amino]propyl]phenyl] dibenzyl phosphate
• CAS: 1268157-70-5
• 化学式: C₃₇H₄₇N₄O₇P
• 分子量: 690.777
• InChiKey: JFWNQIKNDJYOCM-UMSFTDKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-acetyl-O-[bis(benzyloxy)phosphoryl]-N'-{1-[2-(2-oxotetrahydropyrimidin-1(2H)-yl)ethyl]cyclohexyl}-L-tyrosinamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以88%的产率得到N-acetyl-N'-{1-[2-(2-oxotetrahydropyrimidin-1(2H)-yl)ethyl]cyclohexyl}-O-phosphono-Ltyrosinamide
  参考文献：
  名称：

  Development of Non-Peptide Ligands of Growth Factor Receptor-Bound Protein 2-Src Homology 2 Domain Using Molecular Modeling and NMR Spectroscopy

  摘要：

  We report a novel series of non-peptide ligands that inhibit the growth factor receptor-bound protein 2 (Grb2)-Src homology 2 (SH2) domain binding, designed using a combined computational and NMR-driven approach. We have identified a new lead compound, in (IC50 = 56 mu M), which is cytotoxic in HER2-positive breast cancer cells and disrupts the interaction between HER2 and Grb2. Thus, In can be used as a scaffold for the development of efficient Grb2-SH2 domain binding inhibitors.

  DOI：

  10.1021/jm101478n