3'-benzyloxy-3,4'-dimethoxyflavone | 95957-58-7

• 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'-benzyloxy-3,4'-dimethoxyflavone
• 英文别名: 3'-Benzyloxy-3,4'-dimethoxy-flavon；2-(3-benzyloxy-4-methoxy-phenyl)-3-methoxy-chromen-4-one；3-methoxy-2-(4-methoxy-3-phenylmethoxyphenyl)chromen-4-one
• CAS: 95957-58-7
• 化学式: C₂₄H₂₀O₅
• 分子量: 388.42
• InChiKey: JCAPMFGYQXJPGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3'-benzyloxy-3,4'-dimethoxyflavone 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以78%的产率得到2-(3-hydroxy-4-methoxyphenyl)-3-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  3′-Hydroxy-3,4′-dimethoxyflavone blocks tubulin polymerization and is a potent apoptotic inducer in human SK-MEL-1 melanoma cells

  摘要：

  Flavonoids are naturally occurring polyphenolic compounds and are among the most promising anticancer agents. A series of flavonols and their 3-methyl ether derivatives were synthesized and assessed for cytotoxicity. It was found that 3'-hydroxy-3,4'-dimethoxyflavone (flavonoid 7a) displayed strong cytotoxicity against human SK-MEL-1 melanoma cells and blocked tubulin polymerization, but had no significant cytotoxic effects against quiescent or proliferating human peripheral blood mononuclear cells. Our analyses showed that flavonoid 7a induces G2-M cell cycle arrest and apoptosis in melanoma cells which is associated with cytochrome c release and activation of both extrinsic and intrinsic apoptotic pathways of cell death. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.09.043
• 作为产物：
  描述：

  3-苄氧基-4-甲氧基苯甲醛 在 双氧水 、 potassium carbonate 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 、 丙酮 为溶剂， 生成 3'-benzyloxy-3,4'-dimethoxyflavone
  参考文献：
  名称：

  3′-Hydroxy-3,4′-dimethoxyflavone blocks tubulin polymerization and is a potent apoptotic inducer in human SK-MEL-1 melanoma cells

  摘要：

  Flavonoids are naturally occurring polyphenolic compounds and are among the most promising anticancer agents. A series of flavonols and their 3-methyl ether derivatives were synthesized and assessed for cytotoxicity. It was found that 3'-hydroxy-3,4'-dimethoxyflavone (flavonoid 7a) displayed strong cytotoxicity against human SK-MEL-1 melanoma cells and blocked tubulin polymerization, but had no significant cytotoxic effects against quiescent or proliferating human peripheral blood mononuclear cells. Our analyses showed that flavonoid 7a induces G2-M cell cycle arrest and apoptosis in melanoma cells which is associated with cytochrome c release and activation of both extrinsic and intrinsic apoptotic pathways of cell death. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2017.09.043