3-imino-5-phenyl-N-(pyridin-3-yl)-3,5-dihydrophenazin-2-amine | 1401207-19-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-imino-5-phenyl-N-(pyridin-3-yl)-3,5-dihydrophenazin-2-amine
• 英文别名: 3-imino-5-phenyl-N-pyridin-3-ylphenazin-2-amine
• CAS: 1401207-19-9
• 化学式: C₂₃H₁₇N₅
• 分子量: 363.421
• InChiKey: FLJGEGCHDSUPSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-imino-5-phenyl-N-(pyridin-3-yl)-3,5-dihydrophenazin-2-amine 在 盐酸 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 24.0h， 生成 3-{[4-(octahydro-1H-quinolizin-9a-yl)butyl]imino}-5-phenyl-N-(pyridin-3-yl)-3,5-dihydrophenazin-2-amine dihydrochloride
  参考文献：
  名称：

  Clofazimine analogs with antileishmanial and antiplasmodial activity

  摘要：

  A set of novel riminophenazine derivatives has been synthesized and evaluated for in vitro activity against chloroquine-sensitive (CQ-S) and chloroquine-resistant (CQ-R) strains of Plasmodium falciparum and against different species of Leishmania promastigotes. Most of the new compounds inhibited the growth of Leishmania promastigotes as well as CQ-S and CQ-R strains of P. falciparum with IC50 in submicromolar range, resulting in the best cases 1-2 orders of magnitude more potent than the parent compound clofazimine. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.11.028
• 作为产物：
  描述：

  邻氨基二苯胺 在 palladium 10% on activated carbon 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 41.0h， 生成 3-imino-5-phenyl-N-(pyridin-3-yl)-3,5-dihydrophenazin-2-amine
  参考文献：
  名称：

  Identification of Less Lipophilic Riminophenazine Derivatives for the Treatment of Drug-Resistant Tuberculosis

  摘要：

  Clofazimine (CFZ), a member of the riminophenazine class, has been studied in clinical trials for the treatment of multidrug-resistant tuberculosis (MDR-TB). CFZ has several side effects which can be attributed to its extremely high lipophilicity. A series of novel riminophenazine analogues bearing a C-2 pyridyl substituent was designed and synthesized with the goal of maintaining potent activity against Mycobacterium tuberculosis (M. tuberculosis) while improving upon its safety profile by lowering the lipophilicity. All compounds were evaluated for their in vitro activity and cytotoxicity. The results demonstrated that many new compounds had potent activity against M. tuberculosis with MICs of less than 0.03 mu g/mL and low cytotoxicity with IC50 values greater than 64 mu g/mL. Some compounds were tested for in vivo efficacy against MDR-TB in an experimental mouse infection model. Two compounds demonstrated equivalent or better efficacy than CFZ in this model with significantly reduced skin discoloration potential.

  DOI：

  10.1021/jm300828h