3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one | 52259-72-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one
• 英文别名: norfagaronine；3,8,9-trimethoxy-benzo[c]phenanthridin-2-ol；2-Hydroxy-3,8,9-trimethoxybenzophenanthridin；N-Demethyl-fagaronin；N-Dimethyl-fagaronin
• CAS: 52259-72-0
• 化学式: C₂₀H₁₇NO₄
• 分子量: 335.359
• InChiKey: FQLWLTBQJXDYHM-UHFFFAOYSA-N

物化性质

• 沸点：
  568.8±45.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  60.81
• 氢给体数：
  1.0
• 氢受体数：
  5.0

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  甲磺酸甲酯 、 3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one 以49%的产率得到fagaronine mesylate
  参考文献：
  名称：

  Short synthesis and antimalarial activity of fagaronine

  摘要：

  Herein, we report a new synthesis of fagaronine 1, inspired by the synthesis reported by Luo for nornitidine. The in vitro biological activity of fagaronine against malaria on several chloroquine-sensitive and resistant Plasmodium falciparum strains was confirmed, and the selectivity index compared to mammalian cells was calculated. Fagaronine was found to have very good antimalarial activity in vivo, comparable to the activity of the reference compound chloroquine. Therefore, fagaronine appears to be a good potential lead for the design of new antimalarial molecules. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.061
• 作为产物：
  描述：

  N-[(3,4-二甲氧基苯基)甲基]乙酰胺 在 palladium on activated charcoal 盐酸 、 air 、 potassium tert-butylate 、 mercury(II) diacetate 、 氨 、 氢溴酸 、 碘 、 sodium chloride 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 19.42h， 生成 3,8,9-trimethoxy-5H-benzo[c]phenanthridin-2-one
  参考文献：
  名称：

  Studies in SRN1 series. Part 14. Direct synthesis of benzo[c]phenanthridines and benzo[c]phenanthridones via SRN1 reactions

  摘要：

  DOI：

  10.1021/jo00224a057

文献信息

• Studies in SRN1 series. Part 14. Direct synthesis of benzo[c]phenanthridines and benzo[c]phenanthridones via SRN1 reactions
  作者：Rene Beugelmans、Jacqueline Chastanet、Helene Ginsburg、Leticia Quintero-Cortes、Georges Roussi

  DOI：10.1021/jo00224a057

  日期：1985.11
• Short synthesis and antimalarial activity of fagaronine
  作者：M. Rivaud、A. Mendoza、M. Sauvain、A. Valentin、V. Jullian

  DOI：10.1016/j.bmc.2012.05.061

  日期：2012.8

  Herein, we report a new synthesis of fagaronine 1, inspired by the synthesis reported by Luo for nornitidine. The in vitro biological activity of fagaronine against malaria on several chloroquine-sensitive and resistant Plasmodium falciparum strains was confirmed, and the selectivity index compared to mammalian cells was calculated. Fagaronine was found to have very good antimalarial activity in vivo, comparable to the activity of the reference compound chloroquine. Therefore, fagaronine appears to be a good potential lead for the design of new antimalarial molecules. (C) 2012 Elsevier Ltd. All rights reserved.