2,3-methylenedioxy-9,10-dimethoxy-7-n-butyltetrahydroprotoberberine bromide | 69731-09-5

• 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: 2,3-methylenedioxy-9,10-dimethoxy-7-n-butyltetrahydroprotoberberine bromide
• 英文别名: 13-Butyl-16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-2,4(8),9,15(20),16,18-hexaene;bromide
• CAS: 69731-09-5
• 化学式: Br*C₂₄H₃₀NO₄
• 分子量: 476.411
• InChiKey: CRMYGXCMMRSUSX-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.41
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  正溴丁烷 、 四氢小檗碱 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以22%的产率得到2,3-methylenedioxy-9,10-dimethoxy-7-n-butyltetrahydroprotoberberine bromide
  参考文献：
  名称：

  Berberine Analogues as a Novel Class of the Low-Density-Lipoprotein Receptor Up-Regulators: Synthesis, Structure−Activity Relationships, and Cholesterol-Lowering Efficacy

  摘要：

  Twenty-nine derivatives of berberine (1) or pseudoberberine (2) were designed, semisynthesized, and evaluated for their up-regulatory activity on the low-density-lipoprotein receptor (LDLR) expression. SAR analysis revealed that (i) the methylenedioxy group at the 2- and 3-position is an essential element to keep the activity, (ii) the 7-position quaternary ammonium and planar structure of the compound are activity-required, and (iii) addition of electron-donating groups at the 7- or 13-position reduced the activity. Of the compound I analogues, compound 2 exhibited an increased activity on LDLR expression compared to 1. In the hyperlipidemic rats, compound 2 (100 (mg/kg)/day) reduced blood CHO and LDL-c by 42.6% and 49.4%, respectively, more efficient than I did (p < 0.01 for both). The results were confirmed in the hyperlipidemic mice. LD50 of 2 in mice was over 5000 mg/kg (oral). We consider compound 2 a promising cholesterol-lowering drug candidate.

  DOI：

  10.1021/jm801157z