tertra-O-acetyleriodictyol | 10210-16-9

• 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: tertra-O-acetyleriodictyol
• 英文别名: eriodictyol tetracetate；(S)-5,7-diacetoxy-2-(3,4-diacetoxy-phenyl)-chroman-4-one；(S)-5,7-Diacetoxy-2-(3,4-diacetoxy-phenyl)-chroman-4-on；Eriodictyol, Derivative of；[2-acetyloxy-4-[(2S)-5,7-diacetyloxy-4-oxo-2,3-dihydrochromen-2-yl]phenyl] acetate
• CAS: 10210-16-9
• 化学式: C₂₃H₂₀O₁₀
• 分子量: 456.406
• InChiKey: ZDLMCGHYUROZBQ-IBGZPJMESA-N

物化性质

• 熔点：
  140.5-141.5 °C
• 沸点：
  637.4±55.0 °C(Predicted)
• 密度：
  1.348±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  乙酸酐 、 圣草酚 以 吡啶 为溶剂， 反应 12.0h， 生成 tertra-O-acetyleriodictyol
  参考文献：
  名称：

  Phenylbenzopyrones structure-activity studies identify betuletol derivatives as potential antitumoral agents

  摘要：

  We have analyzed the cytotoxicity of 22 compounds with a phenylbenzo-gamma-pirone core structure, most of them obtained from natural sources, in five human tumor cell lines (HL-60, A431, SK-OV-3, HeLa and HOS). Betuletot 3-methyl ether and its diacetate were the most cytotoxic compounds. The HL-60 cell line was especially sensitive to these compounds, with IC50 values of approximately I mu M. Treatment of HL-60 cells with betuletol 3-methyl ether was associated with apoptosis induction which was prevented by a non-specific caspase inhibitor (z-VAD-fmk) and also by a specific inhibitor of caspase-8 (z-IETD-fmk) indicating activation of the extrinsic apoptotic pathway. The results suggest that betuletol 3-methyl ether has potential as new anticancer agent. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ejphar.2006.07.020

文献信息

• A Flavonone from Douglas-Fir Heartwood²
  作者：John C. Pew

  DOI：10.1021/ja01189a059

  日期：1948.9
• Phenylbenzopyrones structure-activity studies identify betuletol derivatives as potential antitumoral agents
  作者：Sara Rubio、José Quintana、Mariana López、José Luis Eiroa、Jorge Triana、Francisco Estévez

  DOI：10.1016/j.ejphar.2006.07.020

  日期：2006.10

  We have analyzed the cytotoxicity of 22 compounds with a phenylbenzo-gamma-pirone core structure, most of them obtained from natural sources, in five human tumor cell lines (HL-60, A431, SK-OV-3, HeLa and HOS). Betuletot 3-methyl ether and its diacetate were the most cytotoxic compounds. The HL-60 cell line was especially sensitive to these compounds, with IC50 values of approximately I mu M. Treatment of HL-60 cells with betuletol 3-methyl ether was associated with apoptosis induction which was prevented by a non-specific caspase inhibitor (z-VAD-fmk) and also by a specific inhibitor of caspase-8 (z-IETD-fmk) indicating activation of the extrinsic apoptotic pathway. The results suggest that betuletol 3-methyl ether has potential as new anticancer agent. (c) 2006 Elsevier B.V. All rights reserved.