(S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 2-(tert-butoxycarbonylamino)-3-(1H-indol-3-yl)propanoate | 1158555-83-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 2-(tert-butoxycarbonylamino)-3-(1H-indol-3-yl)propanoate
• 英文别名: [2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] (2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1158555-83-9
• 化学式: C₃₁H₂₈N₂O₁₀
• 分子量: 588.571
• InChiKey: VXSABCCPWGHRDB-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  43
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  188
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  [2-[3,4-bis(phenylmethoxy)phenyl]-5-hydroxy-4-oxo-7-phenylmethoxychromen-3-yl] (2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate 在 10% palladium on carbon 、 氢气 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 3.0h， 生成 (S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 2-(tert-butoxycarbonylamino)-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Discovering novel quercetin-3-O-amino acid-esters as a new class of Src tyrosine kinase inhibitors

  摘要：

  Quercetin-3-O-amino acid-esters, a new type of quercetin derivatives, were successfully prepared for the first time. Different from quercetin, the novel compounds show higher selectivity as inhibitors against Src tyrosine kinase (IC50 values ranging from 3.2 mu M to 9.9 mu M) than against EGFR tyrosine kinase. Molecular docking reveals that both hydrophobic and hydrogen bonding interactions are important to the selectivity. Therefore, this study provides a new promising scaffold for further development of new anticancer drugs targeting Src tyrosine kinase. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.09.051