sodium scutellarin

• 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: sodium scutellarin
• 英文别名: scutellarin sodium salt；sodium;(2S,3S,4S,5R,6S)-6-[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-7-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylate
• 化学式: C₂₁H₁₇O₁₂*Na
• 分子量: 484.349
• InChiKey: DUEWFVRYFYQQSU-ZSESPEEFSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -4.48
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  206
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  sodium scutellarin 、 溴乙烷 在 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以19.8%的产率得到scutellarin ethyl ester
  参考文献：
  名称：

  Prodrugs of scutellarin: Ethyl, benzyl and N,N-diethylglycolamide ester synthesis, physicochemical properties, intestinal metabolism and oral bioavailability in the rats

  摘要：

  In an effort to enhance the oral bioavailability of scutellarin, ethyl, benzyl and N,N-diethylglycolamide ester of scutellarin were synthesized. The hydrolysis of the prodrugs follows first-order kinetics in aqueous solution, and produced a V-shaped pH profile. The N,N-diethylglycolamide ester is highly susceptible to enzymatic hydrolysis in human plasma (t(1/2) approximate to 7 min) with a high stability in aqueous solution (t(1/2) approximate to 16 day, pH 4.2). Compared with the solubility of scutellarin, the solubility of glycolamide ester was about ten times in pH 4.0 buffer, and about thirty five times in water. Its apparent partition coefficient increased significantly from -2.56 to 1.48. Glycolamide ester of scutellarin was chosen to investigate the intestinal metabolism and in vivo bioavailability Degradation studies in the intestinal tract content and homogenates indicated intestinal metabolism before absorption was a crucial obstacle for the prodrug. N,N-Diethylglycolamide ester can be protected from the degradation in the intestinal lumen by an emulsion. A significant increase in the plasma AUC and C-max of the prodrug emulsion was observed in rats, compared with that of the scutellarin-cyclodextrin complex (P < 0.01). The emulsion of N,N-diethylglycolamide ester produces a 1.58-fold enhancement in apparent bioavailability and 1.4-fold increase in the absolute bioavailability compared to the scutallarin-cyclodextrin complex. (c) 2006 Published by Elsevier B.V.

  DOI：

  10.1016/j.ejps.2006.07.007
• 作为产物：
  描述：

  红盏花素 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以95%的产率得到sodium scutellarin
  参考文献：
  名称：

  灯盏花甲素衍生物及其制备方法与用途

  摘要：

  本发明涉及药物化学技术领域，尤其涉及灯盏花甲素衍生物及其制备方法与用途。本发明提供的灯盏花甲素衍生物具有式I所示结构，其水溶性较高，改变了灯盏花甲素不易溶于水的特性。而本发明提供的制备方法以灯盏花甲素为原料，通过无机碱或有机碱反应，生成本发明提供的灯盏花甲素衍生物。该制备方法工艺简单易行。实验表明，本发明提供的灯盏花甲素衍生物对醛糖还原酶的抑制率高于灯盏花甲素，而本发明提供的制备方法制备的灯盏花甲素衍生物纯度大于99％，收率大于79％。

  公开号：

  CN104086611B

文献信息

• 灯盏花甲素衍生物及其制备方法与用途
  申请人：昆药集团股份有限公司

  公开号：CN104086611B

  公开（公告）日：2016-08-24

  本发明涉及药物化学技术领域，尤其涉及灯盏花甲素衍生物及其制备方法与用途。本发明提供的灯盏花甲素衍生物具有式I所示结构，其水溶性较高，改变了灯盏花甲素不易溶于水的特性。而本发明提供的制备方法以灯盏花甲素为原料，通过无机碱或有机碱反应，生成本发明提供的灯盏花甲素衍生物。该制备方法工艺简单易行。实验表明，本发明提供的灯盏花甲素衍生物对醛糖还原酶的抑制率高于灯盏花甲素，而本发明提供的制备方法制备的灯盏花甲素衍生物纯度大于99％，收率大于79％。
• Prodrugs of scutellarin: Ethyl, benzyl and N,N-diethylglycolamide ester synthesis, physicochemical properties, intestinal metabolism and oral bioavailability in the rats
  作者：Feng Cao、Jian-Xin Guo、Qi-Neng Ping、Zheng-Gen Liao

  DOI：10.1016/j.ejps.2006.07.007

  日期：2006.12

  In an effort to enhance the oral bioavailability of scutellarin, ethyl, benzyl and N,N-diethylglycolamide ester of scutellarin were synthesized. The hydrolysis of the prodrugs follows first-order kinetics in aqueous solution, and produced a V-shaped pH profile. The N,N-diethylglycolamide ester is highly susceptible to enzymatic hydrolysis in human plasma (t(1/2) approximate to 7 min) with a high stability in aqueous solution (t(1/2) approximate to 16 day, pH 4.2). Compared with the solubility of scutellarin, the solubility of glycolamide ester was about ten times in pH 4.0 buffer, and about thirty five times in water. Its apparent partition coefficient increased significantly from -2.56 to 1.48. Glycolamide ester of scutellarin was chosen to investigate the intestinal metabolism and in vivo bioavailability Degradation studies in the intestinal tract content and homogenates indicated intestinal metabolism before absorption was a crucial obstacle for the prodrug. N,N-Diethylglycolamide ester can be protected from the degradation in the intestinal lumen by an emulsion. A significant increase in the plasma AUC and C-max of the prodrug emulsion was observed in rats, compared with that of the scutellarin-cyclodextrin complex (P < 0.01). The emulsion of N,N-diethylglycolamide ester produces a 1.58-fold enhancement in apparent bioavailability and 1.4-fold increase in the absolute bioavailability compared to the scutallarin-cyclodextrin complex. (c) 2006 Published by Elsevier B.V.