4-(3,5-diacetoxy-7-(2-methoxy-2-oxoethoxy)-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate | 1144104-71-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 4-(3,5-diacetoxy-7-(2-methoxy-2-oxoethoxy)-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate
• CAS: 1144104-71-1
• 化学式: C₂₆H₂₂O₁₃
• 分子量: 542.453
• InChiKey: QFCKNHXXCNBTMP-UHFFFAOYSA-N

物化性质

• 沸点：
  695.7±55.0 °C(predicted)
• 密度：
  1.45±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  170.94
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  4-(3,5-diacetoxy-7-(2-methoxy-2-oxoethoxy)-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate 在 N-甲基-2-二甲氨基乙酰氧肟酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 12.0h， 以83%的产率得到Methyl 2-[2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-4-oxochromen-7-yl]oxyacetate
  参考文献：
  名称：

  Inhibition of Heat Shock Induction of Heat Shock Protein 70 and Enhancement of Heat Shock Protein 27 Phosphorylation by Quercetin Derivatives

  摘要：

  Inhibitors of heat-induced heat shock protein 70 (HSP70) expression have the potential to enhance the therapeutic effectiveness of heat-induced radiosensitization of tumors. Among known small molecule inhibitors, quercetin has the advantage of being easily modified for structure-activity studies. Herein, we report the ability of five monomethyl and five carbomethoxymethyl derivatives of quercetin to inhibit heat-induced HSP70 expression and enhance HSP27 phosphorylation in human cells. While quercetin and several derivatives inhibit HSP70 induction and enhance HSP27 phosphorylation at Ser78, other analogues selectively inhibit HSP70 induction without enhancing HSP27 phosphorylation that would otherwise aid in cell survival. We also show that good inhibitors of HSP70 induction are also good inhibitors of both CK2 and CamKII, kinases that are known to activate HSP70 expression by phosphorylation of heat shock transcription factor 1. Derivatives that show poor inhibition of either or both kinases are not good inhibitors of HSP70 induction, suggesting that quercetin's effectiveness is due to its ability to inhibit both kinases.

  DOI：

  10.1021/jm801445c
• 作为产物：
  描述：

  [5,7-二乙酰氧基-2-(3,4-二乙酰氧基苯基)-4-氧代苯并吡喃-3-基]乙酸酯 、 溴乙酸甲酯 在 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 为溶剂， 以54%的产率得到4-(3,5-diacetoxy-7-(2-methoxy-2-oxoethoxy)-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate
  参考文献：
  名称：

  Inhibition of Heat Shock Induction of Heat Shock Protein 70 and Enhancement of Heat Shock Protein 27 Phosphorylation by Quercetin Derivatives

  摘要：

  Inhibitors of heat-induced heat shock protein 70 (HSP70) expression have the potential to enhance the therapeutic effectiveness of heat-induced radiosensitization of tumors. Among known small molecule inhibitors, quercetin has the advantage of being easily modified for structure-activity studies. Herein, we report the ability of five monomethyl and five carbomethoxymethyl derivatives of quercetin to inhibit heat-induced HSP70 expression and enhance HSP27 phosphorylation in human cells. While quercetin and several derivatives inhibit HSP70 induction and enhance HSP27 phosphorylation at Ser78, other analogues selectively inhibit HSP70 induction without enhancing HSP27 phosphorylation that would otherwise aid in cell survival. We also show that good inhibitors of HSP70 induction are also good inhibitors of both CK2 and CamKII, kinases that are known to activate HSP70 expression by phosphorylation of heat shock transcription factor 1. Derivatives that show poor inhibition of either or both kinases are not good inhibitors of HSP70 induction, suggesting that quercetin's effectiveness is due to its ability to inhibit both kinases.

  DOI：

  10.1021/jm801445c