4',5,7-triacetoxy-3,6-dimethoxyflavone | 22701-16-2

• 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',5,7-triacetoxy-3,6-dimethoxyflavone
• 英文别名: 3,6-Dimethoxy-5,7,4'-triacetoxy-flavon；5,7-diacetoxy-2-(4-acetoxy-phenyl)-3,6-dimethoxy-chromen-4-one；[4-(5,7-diacetyloxy-3,6-dimethoxy-4-oxochromen-2-yl)phenyl] acetate
• CAS: 22701-16-2
• 化学式: C₂₃H₂₀O₁₀
• 分子量: 456.406
• InChiKey: VNTQYJSVFBOQON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5,7,4'-三羟基-3,6-二甲氧基黄酮 、 乙酸酐 以 吡啶 为溶剂， 反应 12.0h， 生成 7-acetoxy-4',5-dihydroxy-3,6-dimethoxyflavone 、 5,7-diacetoxy-4'-hydroxy-3,6-dimethoxyflavone 、 4',5,7-triacetoxy-3,6-dimethoxyflavone
  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