5,7-Diacetoxy-3,6,4'-trimethoxy-flavon | 27782-55-4

• 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: 5,7-Diacetoxy-3,6,4'-trimethoxy-flavon
• 英文别名: 5,7-diacetoxy-3,6-dimethoxy-2-(4-methoxy-phenyl)-chromen-4-one；5',7'-Diacetylsantin；[5-acetyloxy-3,6-dimethoxy-2-(4-methoxyphenyl)-4-oxochromen-7-yl] acetate
• CAS: 27782-55-4
• 化学式: C₂₂H₂₀O₉
• 分子量: 428.395
• InChiKey: ZZUQTDHYWMIBBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  D-精氨酸,N2-[N-[N-[N-(N-L-酪氨酰甘氨酰)甘氨酰]-L-苯基丙氨酰]-L-亮氨酰]-(9CI) 、 乙酸酐 以 吡啶 为溶剂， 反应 12.0h， 生成 5,7-Diacetoxy-3,6,4'-trimethoxy-flavon
  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

• 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.