3-(2,3-Dihydro-1,4-benzodioxin-6-yl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-(2,3-Dihydro-1,4-benzodioxin-6-yl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: IQRWDOBTUWBMNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  醋谷胺 、 3-(2,3-Dihydro-1,4-benzodioxin-6-yl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以8%的产率得到6-(2,4-dimethoxyphenyl)-4-(3,4-ethylenedioxyphenyl)-1H-pyridin-2-one
  参考文献：
  名称：

  The synthesis of 4,6-diaryl-2-pyridones and their bioactivation in CYP1 expressing breast cancer cells

  摘要：

  As part of a programme to develop anticancer prodrugs which are activated by cytochrome P450 (CYP) 1B1, a library of 4,6-diaryl-2-pyridones was synthesised in yields of 6-60% from the corresponding chalcones. A number of these derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing little toxicity towards a non-tumour breast cell line with no CYP expression. Metabolism studies provided evidence supporting the involvement of CYP1 enzymes in the bioactivation of these compounds.

  DOI：

  10.1016/j.bmcl.2019.03.030
• 作为产物：
  描述：

  1,4-苯并二恶烷-6-甲醛 、 2,4-二甲氧基苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 3-(2,3-Dihydro-1,4-benzodioxin-6-yl)-1-(2,4-dimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  The synthesis of 4,6-diaryl-2-pyridones and their bioactivation in CYP1 expressing breast cancer cells

  摘要：

  As part of a programme to develop anticancer prodrugs which are activated by cytochrome P450 (CYP) 1B1, a library of 4,6-diaryl-2-pyridones was synthesised in yields of 6-60% from the corresponding chalcones. A number of these derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing little toxicity towards a non-tumour breast cell line with no CYP expression. Metabolism studies provided evidence supporting the involvement of CYP1 enzymes in the bioactivation of these compounds.

  DOI：

  10.1016/j.bmcl.2019.03.030