9-O-Octyl-berberine | 27158-98-1

• 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: 9-O-Octyl-berberine
• 英文别名: 17-methoxy-16-octoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene
• CAS: 27158-98-1
• 化学式: C₂₇H₃₂NO₄
• 分子量: 434.555
• InChiKey: ZHBKNDVNMWMDRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  小檗碱 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.1h， 生成 9-O-Octyl-berberine
  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