19-Bromo-17-methoxy-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-octaen-16-ol;chloride | 1413182-42-9

• 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: 19-Bromo-17-methoxy-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-octaen-16-ol;chloride
• 英文别名: 19-bromo-17-methoxy-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-octaen-16-ol;chloride
• CAS: 1413182-42-9
• 化学式: C₁₉H₁₅BrNO₄*Cl
• 分子量: 436.689
• InChiKey: GTESLPRJCHFUJA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.56
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-溴-2-羟基-3-甲氧基苯甲醛 在 盐酸 、 sodium tetrahydroborate 、 copper(II) sulfate 作用下， 以 甲醇 、 水 为溶剂， 反应 13.0h， 生成 19-Bromo-17-methoxy-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-octaen-16-ol;chloride
  参考文献：
  名称：

  Synthesis and structure–activity relationship of berberine analogues in LDLR up-regulation and AMPK activation

  摘要：

  Currently there is no approved medicine for the treatment of metabolic syndrome. A series of new derivatives of berberine (BBR) or pseudoberberine (1) was synthesized and evaluated for their activity on AMP-activated protein kinase (AMPK) activation and up-regulatory low-density-lipoprotein receptor (LDLR) gene expression, respectively. In addition, the four major metabolites of BBR in vivo were also examined for their activity on AMPK in order to further understand the chemical mechanisms responsible for its glucose-lowering efficacy. Among those BBR analogues, compound 1 exhibited the potential effect on AMPK activation and LDLR up-regulation as compared with BBR. The results suggested that compound 1 might be a multiple-target agent for the treatment of metabolic syndrome, and thus was selected as a promising drug candidate for further development. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.029

文献信息

• Synthesis and structure–activity relationship of berberine analogues in LDLR up-regulation and AMPK activation
  作者：Yan-Xiang Wang、Wei-Jia Kong、Ying-Hong Li、Sheng Tang、Zheng Li、Yang-Biao Li、Yong-Qiang Shan、Chong-Wen Bi、Jian-Dong Jiang、Dan-Qing Song

  DOI：10.1016/j.bmc.2012.09.029

  日期：2012.11

  Currently there is no approved medicine for the treatment of metabolic syndrome. A series of new derivatives of berberine (BBR) or pseudoberberine (1) was synthesized and evaluated for their activity on AMP-activated protein kinase (AMPK) activation and up-regulatory low-density-lipoprotein receptor (LDLR) gene expression, respectively. In addition, the four major metabolites of BBR in vivo were also examined for their activity on AMPK in order to further understand the chemical mechanisms responsible for its glucose-lowering efficacy. Among those BBR analogues, compound 1 exhibited the potential effect on AMPK activation and LDLR up-regulation as compared with BBR. The results suggested that compound 1 might be a multiple-target agent for the treatment of metabolic syndrome, and thus was selected as a promising drug candidate for further development. (C) 2012 Elsevier Ltd. All rights reserved.