4-(2,4-dimethoxyphenyl)-6-(3,4-methylenedioxyphenyl)-1H-pyridin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4-(2,4-dimethoxyphenyl)-6-(3,4-methylenedioxyphenyl)-1H-pyridin-2-one
• 英文别名: 6-(1,3-benzodioxol-5-yl)-4-(2,4-dimethoxyphenyl)-1H-pyridin-2-one
• 化学式: C₂₀H₁₇NO₅
• 分子量: 351.359
• InChiKey: BAMQZFKKGBQMPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  醋谷胺 、 1-(1,3-Benzodioxol-5-yl)-3-(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32%的产率得到4-(2,4-dimethoxyphenyl)-6-(3,4-methylenedioxyphenyl)-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

文献信息

• The synthesis of 4,6-diaryl-2-pyridones and their bioactivation in CYP1 expressing breast cancer cells
  作者：Ketan C. Ruparelia、Sabahat Lodhi、Dyan N. Ankrett、Nicola E. Wilsher、Randolph R.J. Arroo、Gerard A. Potter、Kenneth J.M. Beresford

  DOI：10.1016/j.bmcl.2019.03.030

  日期：2019.6

  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.