(+/-)-N-methylboldine trifluoroacetate | 1346153-53-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: (+/-)-N-methylboldine trifluoroacetate
• CAS: 1346153-53-4
• 化学式: C₂F₃O₂*C₂₀H₂₄NO₄
• 分子量: 455.431
• InChiKey: WPRIMFPXGBFSEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  32.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  99.05
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  N-methylboldine trifluoroacetate 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 168.0h， 生成 (+/-)-N-methylboldine trifluoroacetate
  参考文献：
  名称：

  Alkaloids from the Chinese Vine Gnetum montanum

  摘要：

  During a high-throughput screening campaign of a prefractionated natural product library, fractions from the Chinese vine Gnetum montanum showed in vitro activity against Pseudomonas aeruginosa wild-type strain, PAO1. UV-directed isolation of the organic extract from the vine leaves resulted in the purification of the new natural products N-methyllaudanosolinium trifluoroacetate (1), 3'-hydroxy-N,N-dimethylcoclaurinium trifluoroacetate (2), 1,9,10-trihydroxy-2-methoxy-6-methylaporphinium trifluoroacetate (3), and 6a,7-didehydro-1,9,10-trihydroxy-2-methoxy-6-methylaporphinium trifluoroacetate (4). Compound 4 is described here for the first time, and this is the first report of compounds 1-3 as natural products. Compounds 1-3 were found to racemize over time. Starting from commercially available (+)-boldine, through a series of semisynthetic reactions, a mechanism for the racemization of the isolated compounds is proposed. The known natural products (-)-latifolian A (5) and magnocurarine (6) were also isolated during these studies. The antibacterial activity was explained by the presence of 5, which displayed an IC50 value of 9.8 mu M (MIC = 35 mu M).

  DOI：

  10.1021/np200700f