2-[3-(苄氧基)-4-甲氧基苯基]-3,7-二甲氧基-4H-苯并吡喃-4-酮 | 97257-15-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 2-[3-(苄氧基)-4-甲氧基苯基]-3,7-二甲氧基-4H-苯并吡喃-4-酮
• 英文名称: 3'-benzyloxy-3,7,4'-trimethoxyflavone
• 英文别名: 3,4',7-Trimethoxy-3'-benzyloxy-flavon；3,7,4'-Trimethoxy-3'-benzyloxy-flavon；3'-Benzyloxy-3,4',7-trimethoxy-flavon；2-(3-benzyloxy-4-methoxy-phenyl)-3,7-dimethoxy-chromen-4-one；2-(3-Benzyloxy-4-methoxyphenyl)-3,7-dimethoxy-4H-chromen-4-one；3,7-dimethoxy-2-(4-methoxy-3-phenylmethoxyphenyl)chromen-4-one
• CAS: 97257-15-3
• 化学式: C₂₅H₂₂O₆
• 分子量: 418.446
• InChiKey: GNHKQNSNYQHQOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  2-[3-(苄氧基)-4-甲氧基苯基]-3,7-二甲氧基-4H-苯并吡喃-4-酮 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以75%的产率得到2-(3-羟基-4-甲氧基苯基)-3,7-二甲氧基-4H-苯并吡喃-4-酮
  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-benzyloxy-4,4'-dimethoxy-2'-hydroxychalcone 在 双氧水 、 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 生成 2-[3-(苄氧基)-4-甲氧基苯基]-3,7-二甲氧基-4H-苯并吡喃-4-酮
  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

文献信息

• 3′-Hydroxy-3,4′-dimethoxyflavone blocks tubulin polymerization and is a potent apoptotic inducer in human SK-MEL-1 melanoma cells
  作者：Francisco Estévez-Sarmiento、Mercedes Said、Ignacio Brouard、Francisco León、Celina García、José Quintana、Francisco Estévez

  DOI：10.1016/j.bmc.2017.09.043

  日期：2017.11

  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.

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