8-octadecylberberine chloride | 1314000-34-4

• 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: 8-octadecylberberine chloride
• 英文别名: 8-Octadecyl-berberine chloride；16,17-dimethoxy-14-octadecyl-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;chloride
• CAS: 1314000-34-4
• 化学式: C₃₈H₅₄NO₄*Cl
• 分子量: 624.304
• InChiKey: RBQUOYXDYHHAOF-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  44
• 可旋转键数：
  19
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  盐酸小檗碱 在 溴 、 magnesium 、 溶剂黄146 、 silver(I) chloride 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 4.0h， 生成 8-octadecylberberine chloride
  参考文献：
  名称：

  Synthesis and antihyperlipidemic efficiency of berberine-based HMG-CoA reductase inhibitor

  摘要：

  From more than 100 simulation-designed compounds, 8-alkyl-berberine derivatives with a long aliphatic chain (n = 10-20) were chosen and successfully synthesized to evaluate their antihyperlipidemic activity. With elongating the aliphatic chain, the inhibition of derivatives to HMG-CoA reductase (HMGR) and the LD50 increased gradually. Especially, 8-hexadecyl-berberine (4D) with 8.0 mu mol/l significantly inhibited HMGR, even higher than lovastatin. Then, the inhibition gradually decreased with the aliphatic chain further elongating. Animal experiments showed that all tested derivatives could improve blood lipid level to different degree. Similarly, compound 4D showed the best lipid-reducing efficiency especially for TC and LDL-c level which were near to those of the normal control, and could recover the liver damage caused by the high-fat and high-cholesterol diet. The interaction between the receptor and the ligand indicated that the improved antihyperlipidemic efficiency of 4D was exerted by a dual mechanism of inhibiting HMGR activity similar with statins and lowering the level of low density lipoprotein-cholesterol (LDL-c) similar with berberine. Thus, it might be a potential antihyperlipidemic drug candidate.

  DOI：

  10.1007/s00044-011-9651-z

文献信息

• Synthesis and antihyperlipidemic efficiency of berberine-based HMG-CoA reductase inhibitor
  作者：Xiaoli Ye、Kai He、Xiaokang Zhu、Baoshun Zhang、Xin Chen、Jun Yi、Xuegang Li

  DOI：10.1007/s00044-011-9651-z

  日期：2012.7

  From more than 100 simulation-designed compounds, 8-alkyl-berberine derivatives with a long aliphatic chain (n = 10-20) were chosen and successfully synthesized to evaluate their antihyperlipidemic activity. With elongating the aliphatic chain, the inhibition of derivatives to HMG-CoA reductase (HMGR) and the LD50 increased gradually. Especially, 8-hexadecyl-berberine (4D) with 8.0 mu mol/l significantly inhibited HMGR, even higher than lovastatin. Then, the inhibition gradually decreased with the aliphatic chain further elongating. Animal experiments showed that all tested derivatives could improve blood lipid level to different degree. Similarly, compound 4D showed the best lipid-reducing efficiency especially for TC and LDL-c level which were near to those of the normal control, and could recover the liver damage caused by the high-fat and high-cholesterol diet. The interaction between the receptor and the ligand indicated that the improved antihyperlipidemic efficiency of 4D was exerted by a dual mechanism of inhibiting HMGR activity similar with statins and lowering the level of low density lipoprotein-cholesterol (LDL-c) similar with berberine. Thus, it might be a potential antihyperlipidemic drug candidate.