3-(4-hydroxyphenyl)-6-isopentenyl-7-methoxy-4H-chromen-4-one | 1348361-30-7

• 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: 3-(4-hydroxyphenyl)-6-isopentenyl-7-methoxy-4H-chromen-4-one
• CAS: 1348361-30-7
• 化学式: C₂₁H₂₀O₄
• 分子量: 336.387
• InChiKey: SINDYFJIZKBPNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  59.67
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxyphenyl)-6-isopentenyl-7-methoxy-4H-chromen-4-one 在 L-Selectride 、 potassium carbonate 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 4.0h， 生成 7-methoxy-3-(4-(methoxymethoxy)phenyl)-6-(isopentenyl)chroman-4-one
  参考文献：
  名称：

  Bavachinin analogues as agonists of pan-peroxisome proliferator-activated receptors

  摘要：

  Peroxisome proliferator-activated receptors (PPARs) agonists contribute to the regulation of glucose, lipid, and cholesterol metabolism and have emerged as key targets to treat metabolic syndrome. In our previous study, the natural compound bavachinin was found to have pan-PPAR agonist activity. In this study, five isoflavones, three isoflavanones, and five scaffold-hopping analogues of bavachinin were designed, synthesised, and evaluated through reporter gene assays for pan-PPAR agonist activity. The analogue 2-(4-hydroxyphenyl)-6-isopentenyl-7-methoxy-2,3-dihydroquinolin-4(1H)-one (21) was identified as a pan-PPAR agonist, exhibiting substantially higher PPAR alpha/beta agonist activity and equal PPAR-gamma agonist activity than does bavachinin.

  DOI：

  10.1007/s00044-018-2197-6
• 作为产物：
  描述：

  丹皮酚 在 碘 、 palladium diacetate 、 sodium carbonate 、 potassium carbonate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 50.0h， 生成 3-(4-hydroxyphenyl)-6-isopentenyl-7-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  Bavachinin analogues as agonists of pan-peroxisome proliferator-activated receptors

  摘要：

  Peroxisome proliferator-activated receptors (PPARs) agonists contribute to the regulation of glucose, lipid, and cholesterol metabolism and have emerged as key targets to treat metabolic syndrome. In our previous study, the natural compound bavachinin was found to have pan-PPAR agonist activity. In this study, five isoflavones, three isoflavanones, and five scaffold-hopping analogues of bavachinin were designed, synthesised, and evaluated through reporter gene assays for pan-PPAR agonist activity. The analogue 2-(4-hydroxyphenyl)-6-isopentenyl-7-methoxy-2,3-dihydroquinolin-4(1H)-one (21) was identified as a pan-PPAR agonist, exhibiting substantially higher PPAR alpha/beta agonist activity and equal PPAR-gamma agonist activity than does bavachinin.

  DOI：

  10.1007/s00044-018-2197-6