5'-methoxyhydnocarpin-D

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 黄酮木脂素
• 英文名称: 5'-methoxyhydnocarpin-D
• 英文别名: 5,7-dihydroxy-2-[(2S,3S)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]chromen-4-one
• 化学式: C₂₆H₂₂O₁₀
• 分子量: 494.455
• InChiKey: XBXVVTMNRUIPIX-OZXSUGGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  144
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  木犀草素 、 反式芥子醇 在 silver carbonate 作用下， 以 丙酮 、 苯 为溶剂， 反应 10.0h， 以0.033 g的产率得到5'-methoxyhydnocarpin-D
  参考文献：
  名称：

  Flavonolignan and Flavone Inhibitors of a Staphylococcus aureus Multidrug Resistance Pump:  Structure−Activity Relationships

  摘要：

  Although some progress has been reported on structure-activity relationships (SARs) for inhibitors of mammalian P-glycoprotein MDR efflux pumps, there is almost nothing in the literature regarding SARs for inhibitors of any bacterial efflux pump. Indeed, only a few of these have been described. Our discovery of a potent naturally occurring flavonolignan inhibitor of the NorA MDR pump of Staphylococcus aureus provided a structural foundation upon which SARs could be assessed via synthetic analogues. Several flavonolignans were prepared which proved to have greater potency than the natural isolate, 5'-methoxyhydnocarpin-D, while others showed decreased potency. Surprisingly, some simple alkylated flavones also were quite active MDR pump inhibitors. Variability of activity among the compounds tested was sufficient so that at least some SARs could be postulated and compared with those known for P-glycoprotein.

  DOI：

  10.1021/jm0004190

文献信息

• Flavonolignan and Flavone Inhibitors of a <i>Staphylococcus </i><i>a</i><i>ureus</i> Multidrug Resistance Pump:  Structure−Activity Relationships
  作者：Nathan R. Guz、Frank R. Stermitz、Jeffrey B. Johnson、Teresa D. Beeson、Seth Willen、Jen-Fang Hsiang、Kim Lewis

  DOI：10.1021/jm0004190

  日期：2001.1.1

  Although some progress has been reported on structure-activity relationships (SARs) for inhibitors of mammalian P-glycoprotein MDR efflux pumps, there is almost nothing in the literature regarding SARs for inhibitors of any bacterial efflux pump. Indeed, only a few of these have been described. Our discovery of a potent naturally occurring flavonolignan inhibitor of the NorA MDR pump of Staphylococcus aureus provided a structural foundation upon which SARs could be assessed via synthetic analogues. Several flavonolignans were prepared which proved to have greater potency than the natural isolate, 5'-methoxyhydnocarpin-D, while others showed decreased potency. Surprisingly, some simple alkylated flavones also were quite active MDR pump inhibitors. Variability of activity among the compounds tested was sufficient so that at least some SARs could be postulated and compared with those known for P-glycoprotein.