4',5-dihydroxy-7-methoxyisoflavone-3'-sulfonic acid

• 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: 4',5-dihydroxy-7-methoxyisoflavone-3'-sulfonic acid
• 英文别名: 2-Hydroxy-5-(5-hydroxy-7-methoxy-4-oxochromen-3-yl)benzenesulfonic acid；2-hydroxy-5-(5-hydroxy-7-methoxy-4-oxochromen-3-yl)benzenesulfonic acid
• 化学式: C₁₆H₁₂O₈S
• 分子量: 364.332
• InChiKey: VSKYLIZYZIWDQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  139
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  染料木素 在 硫酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.5h， 生成 4',5-dihydroxy-7-methoxyisoflavone-3'-sulfonic acid
  参考文献：
  名称：

  Genistein derivatives as selective estrogen receptor modulators: Sonochemical synthesis and in vivo anti-osteoporotic action

  摘要：

  Genistein derivatives were synthesized from genistein through a facile sonochemical approach in high yields. The bioassay was performed on ovariectomized (OVX) rats in terms of bone mineral density (BMD) and the weight of bone ash (WBA) to lead to the discovery of eight novel genistein-based selective estrogen receptor modulators. Attention to the structure activity relationship disclosed that the newly introduced 2-hydroxyethylthio scaffolds were essential for the anti-ostcoporotic activity. Moreover, the anti-osteoporotic action of genistein, deprivable by methylation, could be restored and enhanced by subsequent sulfonation. The most promising compound was 4',5.7-tri[3-(2-hydroxyethylthio)propoxy]isoflavone displaying 24% (or 8%) increment in BMD and 31% (or 11%) increase in WBA of the femora relative to those discerned with the OVX (Or genistein) group. Acute toxicity test showed that none of the active compounds was acutely toxic. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.082

文献信息

• Genistein derivatives as selective estrogen receptor modulators: Sonochemical synthesis and in vivo anti-osteoporotic action
  作者：Shi F. Wang、Qing Jiang、Yong H. Ye、Yang Li、Ren X. Tan

  DOI：10.1016/j.bmc.2005.04.082

  日期：2005.8

  Genistein derivatives were synthesized from genistein through a facile sonochemical approach in high yields. The bioassay was performed on ovariectomized (OVX) rats in terms of bone mineral density (BMD) and the weight of bone ash (WBA) to lead to the discovery of eight novel genistein-based selective estrogen receptor modulators. Attention to the structure activity relationship disclosed that the newly introduced 2-hydroxyethylthio scaffolds were essential for the anti-ostcoporotic activity. Moreover, the anti-osteoporotic action of genistein, deprivable by methylation, could be restored and enhanced by subsequent sulfonation. The most promising compound was 4',5.7-tri[3-(2-hydroxyethylthio)propoxy]isoflavone displaying 24% (or 8%) increment in BMD and 31% (or 11%) increase in WBA of the femora relative to those discerned with the OVX (Or genistein) group. Acute toxicity test showed that none of the active compounds was acutely toxic. (c) 2005 Elsevier Ltd. All rights reserved.