2,3-methylenedioxy-9-O-(4-trifluoromethylbenzenesulfonyl)-10-methoxy-13-n-octylprotoberberine chloride | 1375475-72-1

• 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-O-(4-trifluoromethylbenzenesulfonyl)-10-methoxy-13-n-octylprotoberberine chloride
• 英文别名: (17-Methoxy-21-octyl-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-yl) 4-(trifluoromethyl)benzenesulfonate;chloride
• CAS: 1375475-72-1
• 化学式: C₃₄H₃₅F₃NO₆S*Cl
• 分子量: 678.169
• InChiKey: YOZJGXWSHKGZKN-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.78
• 重原子数：
  46
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  盐酸小檗碱 在 吡啶 、 sodium tetrahydroborate 、 potassium carbonate 、 溶剂黄146 、 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 20.0~210.0 ℃ 、5.33 kPa 条件下， 反应 7.5h， 生成 2,3-methylenedioxy-9-O-(4-trifluoromethylbenzenesulfonyl)-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

文献信息

• Synthesis, structure–activity relationship and in vitro anti-mycobacterial evaluation of 13-n-octylberberine derivatives
  作者：Yan-Xin Liu、Chun-Ling Xiao、Yan-Xiang Wang、Ying-Hong Li、Yan-Hui Yang、Yang-Biao Li、Chong-Wen Bi、Li-Mei Gao、Jian-Dong Jiang、Dan-Qing Song

  DOI：10.1016/j.ejmech.2012.03.012

  日期：2012.6

  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.