4-((2R,3R,4S)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxychroman-4-yl)benzene-1,3-diol | 1242246-45-2

• 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: 4-((2R,3R,4S)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxychroman-4-yl)benzene-1,3-diol
• CAS: 1242246-45-2
• 化学式: C₄₉H₄₂O₈
• 分子量: 758.868
• InChiKey: XCLZCQZWPKWVHA-QYFRDPJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.04
• 重原子数：
  57.0
• 可旋转键数：
  14.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  106.84
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4-((2R,3R,4S)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxychroman-4-yl)benzene-1,3-diol 在 30% Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、200.0 kPa 条件下， 反应 4.0h， 以79.6%的产率得到(2R,3R,4S)-4-(2,4-dihydroxyphenyl)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
  参考文献：
  名称：

  Synthesis and ribonuclease A inhibition activity of resorcinol and phloroglucinol derivatives of catechin and epicatechin: Importance of hydroxyl groups

  摘要：

  The reported ribonuclease A inhibitory activity of the green tea extracts prompted us to synthesize novel catechin/epicatechin based conjugates with resorcinol and phloroglucinol with the aim to increase the number of phenolic OH groups. These are found to be more effective inhibitors of ribonuclease A as compared to catechin and epicatechin thus indicating the importance of number of phenolic OH groups for the inhibition of ribonucleolytic activity. Fluorescence studies have been carried out to evaluate the binding parameters. The protein-ligand docking studies are also performed to gain insight into the protein-polyphenols interactions. The epicatechin based polyphenols 1 and 2 also showed inhibition of angiogenin-induced angiogenesis, as determined by chorioallantoic membrane (CAM) assay. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.077
• 作为产物：
  描述：

  (2R,3S,4S)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxychroman-4-yl acetate 、 间苯二酚 在 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 以62%的产率得到4-((2R,3R,4S)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-hydroxychroman-4-yl)benzene-1,3-diol
  参考文献：
  名称：

  Synthesis and ribonuclease A inhibition activity of resorcinol and phloroglucinol derivatives of catechin and epicatechin: Importance of hydroxyl groups

  摘要：

  The reported ribonuclease A inhibitory activity of the green tea extracts prompted us to synthesize novel catechin/epicatechin based conjugates with resorcinol and phloroglucinol with the aim to increase the number of phenolic OH groups. These are found to be more effective inhibitors of ribonuclease A as compared to catechin and epicatechin thus indicating the importance of number of phenolic OH groups for the inhibition of ribonucleolytic activity. Fluorescence studies have been carried out to evaluate the binding parameters. The protein-ligand docking studies are also performed to gain insight into the protein-polyphenols interactions. The epicatechin based polyphenols 1 and 2 also showed inhibition of angiogenin-induced angiogenesis, as determined by chorioallantoic membrane (CAM) assay. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.077