O-[bis(benzyloxy)phosphoryl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-tyrosine | 1268157-63-6

• 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: O-[bis(benzyloxy)phosphoryl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-tyrosine
• 英文别名: Fmoc-D-Tyr(PO3Bn2)-OH；(2R)-3-[4-bis(phenylmethoxy)phosphoryloxyphenyl]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
• CAS: 1268157-63-6
• 化学式: C₃₈H₃₄NO₈P
• 分子量: 663.664
• InChiKey: JSTYRDUOBZALLV-PSXMRANNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(3-aminopropyl)tetrahydropyrimidin-2(1H)-one 、 O-[bis(benzyloxy)phosphoryl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-tyrosine 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.67h， 以81%的产率得到O-[bis(benzyloxy)phosphoryl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-N'-[3-(2-oxotetrahydropyrimidin-1(2H)-yl)propyl]-D-tyrosinamide
  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
• 作为产物：
  描述：

  C₄₄H₄₈NO₇PSi 在 叔丁基过氧化氢 、 水 、 溶剂黄146 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 1.17h， 生成 O-[bis(benzyloxy)phosphoryl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-D-tyrosine
  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