4-(4'-benzyloxyphenyl)-5,6,7-trimethoxychromen-2-one | 635682-36-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: 4-(4'-benzyloxyphenyl)-5,6,7-trimethoxychromen-2-one
• 英文别名: 5,6,7-Trimethoxy-4-(4-phenylmethoxyphenyl)chromen-2-one
• CAS: 635682-36-9
• 化学式: C₂₅H₂₂O₆
• 分子量: 418.446
• InChiKey: FAFMFURKUIEMKO-UHFFFAOYSA-N

物化性质

• 熔点：
  130 °C
• 沸点：
  603.1±55.0 °C(Predicted)
• 密度：
  1.245±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 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

反应信息

• 作为反应物：
  描述：

  4-(4'-benzyloxyphenyl)-5,6,7-trimethoxychromen-2-one 在 氢溴酸 作用下， 反应 12.0h， 以80%的产率得到4-(4'-hydroxyphenyl)-5,6,7-trimethoxy-coumarin
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 4-Arylcoumarin Analogues of Combretastatins

  摘要：

  A series of A-ring polymethoxylated neoflavonoids was prepared by ligand coupling reactions involving either Suzuki or Stille reactions. Cytotoxicity studies indicated a potent activity against a CEM leukemia cell line for the compounds presenting a substitution pattern related to that of combretastatin A-4. The two compounds having a 3'-OH and a 4'-OCH3 substituents on the 4-phenyl B-ring have no effect on human topoisomerases I and II but potently inhibit, in vitro, microtubule assembly. At the cell level, the active compounds were characterized as proapoptotic agents, but they can also trigger cell death via a nonapoptotic pathway.

  DOI：

  10.1021/jm030903d
• 作为产物：
  描述：

  4-hydroxy-5,6,7-trimethoxycoumarin 在 copper(l) iodide 、 四(三苯基膦)钯 、 sodium carbonate 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 1.0h， 生成 4-(4'-benzyloxyphenyl)-5,6,7-trimethoxychromen-2-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 4-Arylcoumarin Analogues of Combretastatins

  摘要：

  A series of A-ring polymethoxylated neoflavonoids was prepared by ligand coupling reactions involving either Suzuki or Stille reactions. Cytotoxicity studies indicated a potent activity against a CEM leukemia cell line for the compounds presenting a substitution pattern related to that of combretastatin A-4. The two compounds having a 3'-OH and a 4'-OCH3 substituents on the 4-phenyl B-ring have no effect on human topoisomerases I and II but potently inhibit, in vitro, microtubule assembly. At the cell level, the active compounds were characterized as proapoptotic agents, but they can also trigger cell death via a nonapoptotic pathway.

  DOI：

  10.1021/jm030903d

文献信息

• Synthesis and Biological Evaluation of 4-Arylcoumarin Analogues of Combretastatins
  作者：Christian Bailly、Christine Bal、Pascale Barbier、Sébastien Combes、Jean-Pierre Finet、Marie-Paule Hildebrand、Vincent Peyrot、Nicole Wattez

  DOI：10.1021/jm030903d

  日期：2003.12.1

  A series of A-ring polymethoxylated neoflavonoids was prepared by ligand coupling reactions involving either Suzuki or Stille reactions. Cytotoxicity studies indicated a potent activity against a CEM leukemia cell line for the compounds presenting a substitution pattern related to that of combretastatin A-4. The two compounds having a 3'-OH and a 4'-OCH3 substituents on the 4-phenyl B-ring have no effect on human topoisomerases I and II but potently inhibit, in vitro, microtubule assembly. At the cell level, the active compounds were characterized as proapoptotic agents, but they can also trigger cell death via a nonapoptotic pathway.