(2R,3R)-2-(3,4-Dihydroxy-phenyl)-3-(3,4,5-trimethoxy-benzyloxy)-chroman-5,7-diol

• 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: (2R,3R)-2-(3,4-Dihydroxy-phenyl)-3-(3,4,5-trimethoxy-benzyloxy)-chroman-5,7-diol
• 英文别名: (2R,3R)-2-(3,4-dihydroxyphenyl)-3-[(3,4,5-trimethoxyphenyl)methoxy]-3,4-dihydro-2H-chromene-5,7-diol
• 化学式: C₂₅H₂₆O₉
• 分子量: 470.476
• InChiKey: ATDKJUKVGVOGDN-DNQXCXABSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  127
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5,7,3',4'-tetra-O-benzylepicatechin 在 palladium on activated charcoal cesium hydroxide 、 氢气 、 四丁基碘化铵 作用下， 生成 (2R,3R)-2-(3,4-Dihydroxy-phenyl)-3-(3,4,5-trimethoxy-benzyloxy)-chroman-5,7-diol
  参考文献：
  名称：

  Anticancer activity of 3-O-acyl and alkyl-(−)-epicatechin derivatives

  摘要：

  By changing the structure or replacing the gallate group of (-)-ECG, 3-O-acyl and alkyl-(-)-epicatechin derivatives were synthesized to be screen as anticancer agents using the MTT assay in vitro against cancer cell lines (PC3, SKOV3, U373MG). 3-O-Acyl and alkyl-(-)-epicatechin derivatives (4-25) exhibited better anticancer activity than (-)-ECG and specially, compounds 6-8, 17-19, which were modified aliphatic chains with moderate sizes (C8-C12) showed strong anticancer activity (IC50 = 6.4-31.2 muM). The introduction of an alkyloxy group on 3-O-hydroxyl instead of an acyloxy group significantly enhanced inhibitory activity. Consequently, the compound that showed the most potency as anticancer agents were 3-O-decyl-(-)-epicatechin (18) (IC50 = 8.9, 7.9, 6.4 muM against PC3, SKOV3, U373MG, respectively), which modified the appropriate lipophilic group on the C-3 hydroxyl as an alkyloxy group. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.063

文献信息

• Anticancer activity of 3-O-acyl and alkyl-(−)-epicatechin derivatives
  作者：Ki Duk Park、Sul Gi Lee、Sung Uk Kim、Sung Han Kim、Won Suck Sun、Sung Jin Cho、Do Hyeon Jeong

  DOI：10.1016/j.bmcl.2004.07.063

  日期：2004.10

  By changing the structure or replacing the gallate group of (-)-ECG, 3-O-acyl and alkyl-(-)-epicatechin derivatives were synthesized to be screen as anticancer agents using the MTT assay in vitro against cancer cell lines (PC3, SKOV3, U373MG). 3-O-Acyl and alkyl-(-)-epicatechin derivatives (4-25) exhibited better anticancer activity than (-)-ECG and specially, compounds 6-8, 17-19, which were modified aliphatic chains with moderate sizes (C8-C12) showed strong anticancer activity (IC50 = 6.4-31.2 muM). The introduction of an alkyloxy group on 3-O-hydroxyl instead of an acyloxy group significantly enhanced inhibitory activity. Consequently, the compound that showed the most potency as anticancer agents were 3-O-decyl-(-)-epicatechin (18) (IC50 = 8.9, 7.9, 6.4 muM against PC3, SKOV3, U373MG, respectively), which modified the appropriate lipophilic group on the C-3 hydroxyl as an alkyloxy group. (C) 2004 Elsevier Ltd. All rights reserved.