2-hydroxyl-3,9-di-n-butoxy-10-methoxy-13-n-octylprotoberberine chloride | 1375475-84-5

• 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-hydroxyl-3,9-di-n-butoxy-10-methoxy-13-n-octylprotoberberine chloride
• 英文别名: 3,9-Dibutoxy-10-methoxy-13-octyl-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-2-ol;chloride
• CAS: 1375475-84-5
• 化学式: C₃₄H₄₈NO₄*Cl
• 分子量: 570.212
• InChiKey: CNPAXYSXTRCFGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  40
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  盐酸小檗碱 在 aluminum (III) chloride 、 sodium tetrahydroborate 、 potassium carbonate 、 溶剂黄146 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 79.5h， 生成 2-hydroxyl-3,9-di-n-butoxy-10-methoxy-13-n-octylprotoberberine chloride
  参考文献：
  名称：

  Synthesis, structure–activity relationship and in vitro anti-mycobacterial evaluation of 13-n-octylberberine derivatives

  摘要：

  Twenty-eight new 13-n-octylberberine derivatives were synthesized and evaluated for their activities against drug-susceptible Mycobacterium tuberculosis (M. tuberculosis) strain H(37)Rv. Among these compounds, compound 16e was the most effective anti-tubercular agent with a MIC value of 0.125 mu g/mL Importantly, compound 16e exhibited more potent effect against rifampicin (RIF)- and isoniazid (INH)-resistant M. tuberculosis strains than both RIF and INN, suggesting a new mechanism of action. Therefore, it has been selected as a drug candidate for further investigation, or as a chemical probe for identifying protein target and studying tuberculosis biology. We consider 13-n-octylberberine analogs to be a promising novel class of antituberculars against multi-drug-resistant (MDR) strains of M. tuberculosis. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.012