quercetin 3,3'-di-O-methyl ether triacetate | 26305-93-1

• 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: quercetin 3,3'-di-O-methyl ether triacetate
• 英文别名: 5,7-diacetoxy-2-(4-acetoxy-3-methoxy-phenyl)-3-methoxy-chromen-4-one；5,7-Diacetoxy-2-(4-acetoxy-3-methoxy-phenyl)-3-methoxy-chromen-4-on；3,3'-O-Dimethyl-5,7,4'-O-triacetyl-quercetin；[4-(5,7-Diacetyloxy-3-methoxy-4-oxochromen-2-yl)-2-methoxyphenyl] acetate
• CAS: 26305-93-1
• 化学式: C₂₃H₂₀O₁₀
• 分子量: 456.406
• InChiKey: WXOJXOAMTYNWQY-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：

  3,3'-二-O-甲基槲皮素 、 乙酸酐 以 吡啶 为溶剂， 反应 16.0h， 生成 quercetin 3,3'-di-O-methyl ether triacetate
  参考文献：
  名称：

  来自 Wedelia biflora 叶子的潜在农用化学品

  摘要：

  摘要 藜芦酰肼、3,3'-二-O-甲基槲皮素、2,7-二羟基-3(3t'-甲氧基-4'-羟基)-5-甲氧基异黄酮和3',7-二-O-甲基槲皮素四种化合物从 Wedelia biflora 干叶的二氯甲烷提取物中分离得到。从光谱证据阐明了这些结构。第三种化合物具有抗真菌和棉铃象甲拒食活性，而第四种化合物具有抗真菌活性。

  DOI：

  10.1016/0031-9422(93)85152-h

文献信息

• 175. Flavonols from the bark of Melicope ternata. Part III. A synthesis of quercetin 3 : 3′-dimethyl ether, quercetin 3 : 7 : 3′-trimethyl ether, quercetin 3 : 5 : 7 : 3′-tetramethyl ether, ternatin, and related benzyl ethers
  作者：Lindsay H. Briggs、R. H. Locker

  DOI：10.1039/jr9500000864

  日期：——
• 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.