10-methoxy-9-(((2S,3S,4R,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium | 1310674-55-5

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: 10-methoxy-9-(((2S,3S,4R,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium
• CAS: 1310674-55-5
• 化学式: C₂₄H₂₄NO₈
• 分子量: 454.456
• InChiKey: TXVSGSHYYXSCHF-INYSMAPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  33.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  110.72
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  小檗碱 在 碳酸氢钠 、 sodium carbonate 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 10-methoxy-9-(((2S,3S,4R,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium
  参考文献：
  名称：

  Synthesis of 9-O-glycosyl-berberine derivatives and bioavailability evaluation

  摘要：

  To increase the bioavailability of berberine, three new 9-O-glycosyl-berberine derivatives, 9-O-glucosyl-(4a), 9-O-arabinosyl-(4b), and 9-O-erythrol-(4c) were obtained and confirmed by UV, (HNMR)-H-1, (CNMR)-C-13, and MS. The pharmacokinetic profiles of these synthetic compounds have been evaluated compared with berberine (1) and 9-O-alkyl-berberine (5) derivatives, which showed that maximum concentration (C (max)) and area under concentration-time curve (AUC) of 9-O-glycosyl-berberine increased dramatically. The results indicated that hydrophilic modification could significantly improve the bioavailability of berberine; 9-O-glycosyl-berberine might be a promising prodrug.

  DOI：

  10.1007/s00044-011-9678-1