9-amino-5-(pyridin-4-ylimino)-5H-benzo[a]phenoxazine | 1616349-75-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 9-amino-5-(pyridin-4-ylimino)-5H-benzo[a]phenoxazine
• 英文别名: 5-(4-Pyridylimino)benzo[a]phenoxazin-9-amine；5-pyridin-4-yliminobenzo[a]phenoxazin-9-amine
• CAS: 1616349-75-7
• 化学式: C₂₁H₁₄N₄O
• 分子量: 338.368
• InChiKey: BKTTXGRARKKJNK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  darrow red 、 4-氯吡啶盐酸盐 在 吡啶盐酸盐 、 锌 作用下， 以 乙二醇 为溶剂， 反应 4.0h， 以35%的产率得到9-amino-5-(pyridin-4-ylimino)-5H-benzo[a]phenoxazine
  参考文献：
  名称：

  Novel synthetic route for antimalarial benzo[a]phenoxazine derivative SSJ-183 and two active metabolites

  摘要：

  A productive synthesis of benzo[a]phenoxazine derivative SSJ-183 (1), a promising lead for antimalarial agents, was developed using a one pot procedure. Furthermore, N-deethylated metabolite 3 and bis-N,N-deethylated metabolite 4 were synthesized by the application of the method. The metabolites 3 and 4 showed comparable and ∼2-fold increased activities against drug-sensitive and drug-resistant Plasmodium falciparum parasites.

  DOI：

  10.1016/j.bmc.2014.04.066

文献信息

• Novel synthetic route for antimalarial benzo[a]phenoxazine derivative SSJ-183 and two active metabolites
  作者：Yuki Mizukawa、Jian-Feng Ge、Abu Bakar Md、Isamu Itoh、Christian Scheurer、Sergio Wittlin、Reto Brun、Hiroyuki Matsuoka、Masataka Ihara

  DOI：10.1016/j.bmc.2014.04.066

  日期：2014.7

  A productive synthesis of benzo[a]phenoxazine derivative SSJ-183 (1), a promising lead for antimalarial agents, was developed using a one pot procedure. Furthermore, N-deethylated metabolite 3 and bis-N,N-deethylated metabolite 4 were synthesized by the application of the method. The metabolites 3 and 4 showed comparable and ∼2-fold increased activities against drug-sensitive and drug-resistant Plasmodium falciparum parasites.