6-formyl-3-(3,4-dimethoxyphenyl)coumarin

• 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: 6-formyl-3-(3,4-dimethoxyphenyl)coumarin
• 英文别名: 6-Formyl-3-(3,4-dimethoxy-phenyl)coumarin；3-(3,4-dimethoxyphenyl)-2-oxochromene-6-carbaldehyde
• 化学式: C₁₈H₁₄O₅
• 分子量: 310.306
• InChiKey: IEISJPYJCXXGRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  苄基三苯基氯化膦 、 6-formyl-3-(3,4-dimethoxyphenyl)coumarin 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 以36.7%的产率得到cis-3-(3,4-dimethoxyphenyl)-6-styrylcoumarin
  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：

  3,4-二甲氧基苯乙酰肼 在 N-溴代丁二酰亚胺(NBS) 、 乙酸酐 、 溶剂黄146 、 三乙胺 、 过氧化苯甲酰 作用下， 以 苯 为溶剂， 反应 16.0h， 生成 6-formyl-3-(3,4-dimethoxyphenyl)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

文献信息

• Efficient Synthesis of 3‐Substituted Coumarins
  作者：Sabir H. Mashraqui、Dhaval Vashi、Hitesh D. Mistry

  DOI：10.1081/scc-200028575

  日期：2004.1

  The Mukaiyama's esterification protocol, using 2-chloro-1-methylpyridinium iodide-triethylamine reagent, has been successfully exploited to provide rapid access to a variety of 3-substituted coumarins in satisfactory yields.
• Synthesis and biological evaluation of resveratrol–coumarin hybrid compounds as potential antitumor agents
  作者：Wei Shen、Jianfeng Mao、Juan Sun、Minjie Sun、Can Zhang

  DOI：10.1007/s00044-012-0159-y

  日期：2013.4

  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.