3-hydroxy-2-(2-hydroxyphenyl)-7-methoxy-4H-chromen-4-one | 320576-68-9

• 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-hydroxy-2-(2-hydroxyphenyl)-7-methoxy-4H-chromen-4-one
• 英文别名: 3-hydroxy-2-(2-hydroxy-phenyl)-7-methoxy-chromen-4-one；3-Hydroxy-2-(2-hydroxy-phenyl)-7-methoxy-chromen-4-on；3-Hydroxy-2-(2-hydroxyphenyl)-7-methoxychromen-4-one；3-hydroxy-2-(2-hydroxyphenyl)-7-methoxychromen-4-one
• CAS: 320576-68-9
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: ZMGKUWRCRITKDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-hydroxy-2-(2-hydroxyphenyl)-7-methoxy-4H-chromen-4-one 生成 3-acetoxy-2-(2-acetoxy-phenyl)-7-methoxy-chromen-4-one
  参考文献：
  名称：

  2'-羟基-和2'-甲氧基-黄酮

  摘要：

  DOI：

  10.1039/jr9550000166
• 作为产物：
  描述：

  2-苄氧基苯甲醛 在 palladium 10% on activated carbon 、 氢气 、 双氧水 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 为溶剂， 反应 1.0h， 生成 3-hydroxy-2-(2-hydroxyphenyl)-7-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

文献信息

• 2′-Hydroxy- and 2′-methoxy-flavanones
  作者：T. H. Simpson、W. B. Whalley

  DOI：10.1039/jr9550000166

  日期：——
• 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.