甘草素-7,4'-二乙酸酯 | 54301-00-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 甘草素-7,4'-二乙酸酯
• 英文名称: liquiritigenin diacetate
• 英文别名: liquiritigenin-7,4'-diacetate；7,4'-diacetyldihydroflavone；[4-[(2S)-7-acetyloxy-4-oxo-2,3-dihydrochromen-2-yl]phenyl] acetate
• CAS: 54301-00-7
• 化学式: C₁₉H₁₆O₆
• 分子量: 340.332
• InChiKey: ZXYRFBJRBWNPSU-SFHVURJKSA-N

物化性质

• 沸点：
  522.6±50.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  甘草素-7,4'-二乙酸酯 反应 5.0h， 生成 异甘草素
  参考文献：
  名称：

  Synthesis, antitubercular activity, and molecular modeling studies of analogues of isoliquiritigenin and liquiritigenin, bioactive components from Glycyrrhiza glabra

  摘要：

  Isoliquiritigenin (ISL, 1) and liquiritigenin (LTG, 2) were isolated from the rhizomes of Glycyrrhiza glabra. In an attempt to develop potent and selective antituberculosis agents, a series of ISL analogues were synthesized mainly via acid- and base-catalyzed Claisen-Schmidt condensation reaction for their antitubercular activity. Compared to ISL (MIC = 25 mu g/mL), analogues 5, 8, and 10 showed similar antitubercular activity, but, interestingly, 6, 7, and 15 exhibited twofold higher activity (MIC = 12.5 mu g/mL) over ISL, against Mycobacterium tuberculosis. Among the LTG derivatives, LTG 4'-acetate and LTG-oxime were found to be as active (MIC = 25 mu g/mL) as LTG. It is the first report on antimycobacterial activity of these ISL- and LTG-based derivatives. Molecular docking and in silico ADME studies revealed that compounds 6, 7, and 15 are potent inhibitors of M. tuberculosis H(37)Rv alanine dehydrogenase and showed compliance with standard parameters of drug likeness.

  DOI：

  10.1007/s00044-015-1401-1
• 作为产物：
  描述：

  甘草素 、 乙酸酐 以96%的产率得到甘草素-7,4'-二乙酸酯
  参考文献：
  名称：

  二氢黄酮类化合物及其制备方法和应用

  摘要：

  本发明属于医药技术领域，特别涉及二氢黄酮类化合物及其制备方法和应用。具体公开了式(I)所示的化合物或其药学上可接受的盐。本发明的式(I)化合物可靶向于hURAT1和/或GLUT9，从而促进尿酸排泄，达到降尿酸的效果。可用于制备治疗和/或预防和/或延缓和/或辅助治疗和/或处理与hURAT1/GLUT9活性相关的疾病的药物，在预防或治疗跟高尿酸血症相关的疾病(如痛风、痛风性关节炎、尿酸性肾结石等)方面具有很好的应用前景。

  公开号：

  CN112661738B