3,3',4',8-tetra-O-allylquercetin | 19360-71-5

• 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: 3,3',4',8-tetra-O-allylquercetin
• 英文别名: 3,7-bis-allyloxy-2-(3,4-bis-allyloxy-phenyl)-5-hydroxy-chromen-4-one；3,7,3',4'-Tetra-allyloxy-5-hydroxy-flavon
• CAS: 19360-71-5
• 化学式: C₂₇H₂₆O₇
• 分子量: 462.499
• InChiKey: VKQMOVBBITVLQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  34.0
• 可旋转键数：
  13.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  87.36
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  槲皮素 、 3-溴丙烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 10.0h， 以82.5%的产率得到3,3',4',8-tetra-O-allylquercetin
  参考文献：
  名称：

  Synthesis, characterization, anti-inflammatory and anti-proliferative activity against MCF-7 cells of O-alkyl and O-acyl flavonoid derivatives

  摘要：

  A series of O-alkyl and O-acyl flavonoid derivatives was synthesized in high efficiency. Alkylation and acylation of 5-hydroxyflavonoids showed that the low reactivity hydroxyl group, 5-OH, well reacted with strong reagents whereas with weaker reagents, the different products were obtained dependently on structural characteristic of ring C of respective flavonoid. In order to evaluate anti-inflammatory activity, all compounds were tested for in vitro inhibition of bovine serum albumin denaturation and in vivo inhibition of carrageenan-induced mouse paw edema. Among them, the compounds 3, 3b, 4b and 4c demonstrated more effective anti-inflammatory activity than standard drugs (diclofenac sodium and ketoprofen) in both tests. Meanwhile, the flavonoids 2, 2c, 3a and 4b displayed anti-proliferative activity against MCF-7 cell lines. Triacetyl derivative of hesperetin 4b inducing degradation of DNA in MCF-7 cells was observed. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2015.09.005