| 1065581-23-8

• 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
• CAS: 1065581-23-8
• 化学式: C₁₉H₁₆NO₃*HO
• 分子量: 323.348
• InChiKey: YXXQUBRWSLZBIK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  61.57
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 potassium carbonate 、 甲醇 、 calcium oxide 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 水 、 乙醇 为溶剂， 反应 4.5h， 生成 10-methoxy-5,6-dihydro[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium chloride
  参考文献：
  名称：

  Synthesis and structure–activity relationships of berberine analogues as a novel class of low-density-lipoprotein receptor up-regulators

  摘要：

  Berberine (BBR, 1) is a novel cholesterol-lowering agent that up-regulates low-density-lipoprotein receptor (LDLR) expression through a mechanism different from that of statins. Because of the unique mode of action and good safety record, BBR provoked our interest to do structure modification at different domains for its cholesterol-lowering activity. Nineteen BBR analogues with substituents on the benzene ring D were synthesized in the present study. The analysis of structure-activity relationship (SAR) indicated that the two methoxyl groups in an ortho-distribution on this benzene ring afforded a good activity. Among the 19 analogues, compound 8j bearing a methoxyl at both 10- and 11-position showed an increased LDLR up-regulatory activity in respect to BBR, and therefore has been selected as a promising cholesterol-lowering drug candidate for further evaluation. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.005
• 作为产物：
  描述：

  草酸醛 、 2-(1,3-benzodioxol-5-yl)-N-(3-methoxybenzyl)ethanamine 在 盐酸 、 甲酸 、 copper(II) sulfate 、 甲醇 、 calcium oxide 作用下， 以 水 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Synthesis and structure–activity relationships of berberine analogues as a novel class of low-density-lipoprotein receptor up-regulators

  摘要：

  Berberine (BBR, 1) is a novel cholesterol-lowering agent that up-regulates low-density-lipoprotein receptor (LDLR) expression through a mechanism different from that of statins. Because of the unique mode of action and good safety record, BBR provoked our interest to do structure modification at different domains for its cholesterol-lowering activity. Nineteen BBR analogues with substituents on the benzene ring D were synthesized in the present study. The analysis of structure-activity relationship (SAR) indicated that the two methoxyl groups in an ortho-distribution on this benzene ring afforded a good activity. Among the 19 analogues, compound 8j bearing a methoxyl at both 10- and 11-position showed an increased LDLR up-regulatory activity in respect to BBR, and therefore has been selected as a promising cholesterol-lowering drug candidate for further evaluation. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.07.005