7-formyl-3-(4-methoxyphenyl)coumarin | 1387531-17-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-formyl-3-(4-methoxyphenyl)coumarin
• 英文别名: 3-(4-methoxyphenyl)-2-oxochromene-7-carbaldehyde
• CAS: 1387531-17-0
• 化学式: C₁₇H₁₂O₄
• 分子量: 280.28
• InChiKey: CRSHNKVUCSAXTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-formyl-3-(4-methoxyphenyl)coumarin 、 (4-甲氧基苄基)三苯基氯化膦 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以18.2%的产率得到trans-3-(4-methoxyphenyl)-7-(4-methoxystyryl)coumarin
  参考文献：
  名称：

  Synthesis and biological evaluation of resveratrol–coumarin hybrid compounds as potential antitumor agents

  摘要：

  Eighteen resveratrol-coumarin hybrid compounds (6 or 7-styryl-3-phenylcoumarin) were designed, synthesized and thirteen compounds were evaluated for their antitumor activities against MCF-7, HCT-28, and K562 tumor cell lines. Among them, compounds 2Z, 2E, 5E, and 7E showed varying degrees of growth inhibition of the above cell lines (IC50: 3.78-19.16 mu mol/L). On the basis of the biological results, structure-activity relationships were obtained and discussed.

  DOI：

  10.1007/s00044-012-0159-y
• 作为产物：
  描述：

  间甲酚 在 N-溴代丁二酰亚胺(NBS) 、 硼酸 、 乙酸酐 、 溶剂黄146 、 三乙胺 、 过氧化苯甲酰 作用下， 以 甘油 、 苯 为溶剂， 反应 16.17h， 生成 7-formyl-3-(4-methoxyphenyl)coumarin
  参考文献：
  名称：

  Synthesis and biological evaluation of resveratrol–coumarin hybrid compounds as potential antitumor agents

  摘要：

  Eighteen resveratrol-coumarin hybrid compounds (6 or 7-styryl-3-phenylcoumarin) were designed, synthesized and thirteen compounds were evaluated for their antitumor activities against MCF-7, HCT-28, and K562 tumor cell lines. Among them, compounds 2Z, 2E, 5E, and 7E showed varying degrees of growth inhibition of the above cell lines (IC50: 3.78-19.16 mu mol/L). On the basis of the biological results, structure-activity relationships were obtained and discussed.

  DOI：

  10.1007/s00044-012-0159-y