1-[4-(3-oxo-3-phenylpropenyl)phenoxymethyl]benzo[f]chromen-3-one | 1228819-65-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-[4-(3-oxo-3-phenylpropenyl)phenoxymethyl]benzo[f]chromen-3-one
• 英文别名: 1-[[4-(3-oxo-3-phenylprop-1-enyl)phenoxy]methyl]benzo[f]chromen-3-one
• CAS: 1228819-65-5
• 化学式: C₂₉H₂₀O₄
• 分子量: 432.475
• InChiKey: RSCLQAHRPKBRMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.42
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  56.51
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-[4-(3-oxo-3-phenylpropenyl)phenoxymethyl]benzo[f]chromen-3-one 、 硫脲 在 盐酸 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以58%的产率得到1-[4-(2-mercapto-6-phenylpyrimidin-4-yl)phenoxymethyl]benzo[f]chromen-3-one
  参考文献：
  名称：

  Analgesic, anti-pyretic and DNA cleavage studies of novel pyrimidine derivatives of coumarin moiety

  摘要：

  A novel series of 4-[4-(6-phenyl-pyrimidin-4-yl)-phenoxymethyl]-chromen-2-ones [5-7(a e)] were synthesized from various 4-bromomethyl coumarins 1(a e). The synthesized compounds were screened for In-vivo analgesic and anti-pyretic activities at a dose of 25 and 100 mg/kg body weight (b w), respectively. Among them, compounds 5(d), 6(c) and 7(d) exhibited significant analgesic activity comparable with standard drug analgin using Tail-flick model. Compounds 5(a) and 7(a d) showed significant anti-pyretic activities comparable with standard drug aspirin using yeast-induced pyrexia model. DNA cleavage study by agarose gel electrophoresis method was also studied. Qualitative SAR studies indicate that, compounds with amino group at 2-position of pyrimidine ring enhances analgesic and anti-pyretic activities and compounds with hydroxyl and till group at 2-position of pyrimidine ring increase DNA cleavage activities.

  DOI：

  10.1016/j.ejmech.2010.02.048
• 作为产物：
  描述：

  5,6-benzo-4-bromomethylcoumarin 、 2-羟基查耳酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.5h， 以73%的产率得到1-[4-(3-oxo-3-phenylpropenyl)phenoxymethyl]benzo[f]chromen-3-one
  参考文献：
  名称：

  Analgesic, anti-pyretic and DNA cleavage studies of novel pyrimidine derivatives of coumarin moiety

  摘要：

  A novel series of 4-[4-(6-phenyl-pyrimidin-4-yl)-phenoxymethyl]-chromen-2-ones [5-7(a e)] were synthesized from various 4-bromomethyl coumarins 1(a e). The synthesized compounds were screened for In-vivo analgesic and anti-pyretic activities at a dose of 25 and 100 mg/kg body weight (b w), respectively. Among them, compounds 5(d), 6(c) and 7(d) exhibited significant analgesic activity comparable with standard drug analgin using Tail-flick model. Compounds 5(a) and 7(a d) showed significant anti-pyretic activities comparable with standard drug aspirin using yeast-induced pyrexia model. DNA cleavage study by agarose gel electrophoresis method was also studied. Qualitative SAR studies indicate that, compounds with amino group at 2-position of pyrimidine ring enhances analgesic and anti-pyretic activities and compounds with hydroxyl and till group at 2-position of pyrimidine ring increase DNA cleavage activities.

  DOI：

  10.1016/j.ejmech.2010.02.048