2-methyl-3-(oxazolo[4,5-b]pyridin-2-yl)aniline | 328907-88-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-3-(oxazolo[4,5-b]pyridin-2-yl)aniline
• 英文别名: 2-Methyl-3-oxazolo[4,5-b]pyridin-2-yl-phenylamine；2-methyl-3-([1,3]oxazolo[4,5-b]pyridin-2-yl)aniline
• CAS: 328907-88-6
• 化学式: C₁₃H₁₁N₃O
• mdl: MFCD01128393
• 分子量: 225.25
• InChiKey: IPNBOLYXGONZDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  64.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  糠酸（呋喃甲酸） 、 2-methyl-3-(oxazolo[4,5-b]pyridin-2-yl)aniline 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以68%的产率得到N-(2-methyl-3-(oxazolo[4,5-b]pyridin-2-yl)phenyl)furan-2-carboxamide
  参考文献：
  名称：

  3-(Oxazolo[4,5-b]pyridin-2-yl)anilides as a novel class of potent inhibitors for the kinetoplastid Trypanosoma brucei, the causative agent for human African trypanosomiasis

  摘要：

  A whole organism high-throughput screen of approximately 87,000 compounds against Trypanosoma brucei brucei led to the recent discovery of several novel compound classes with low micromolar activity against this organism and without appreciable cytotoxicity to mammalian cells. Herein we report a structure activity relationship (SAR) investigation around one of these hit classes, the 3-(oxazolo[4,5-b] pyridin-2-yl)anilides. Sharp SAR is revealed, with our most active compound (5) exhibiting an IC50 of 91 nM against the human pathogenic strain T.b. rhodesiense and being more than 700 times less toxic towards the L6 mammalian cell line. Physicochemical properties are attractive for many compounds in this series. For the most potent representatives, we show that solubility and metabolic stability are key parameters to target during future optimisation.[GRAPHICS](C) 2013 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2013.05.007
• 作为产物：
  描述：

  2-氨基-3-羟基吡啶 、 2-甲基-3-氨基苯甲酸 在 polyphosphoric acid 作用下， 反应 4.0h， 以48%的产率得到2-methyl-3-(oxazolo[4,5-b]pyridin-2-yl)aniline
  参考文献：
  名称：

  3-(Oxazolo[4,5-b]pyridin-2-yl)anilides as a novel class of potent inhibitors for the kinetoplastid Trypanosoma brucei, the causative agent for human African trypanosomiasis

  摘要：

  A whole organism high-throughput screen of approximately 87,000 compounds against Trypanosoma brucei brucei led to the recent discovery of several novel compound classes with low micromolar activity against this organism and without appreciable cytotoxicity to mammalian cells. Herein we report a structure activity relationship (SAR) investigation around one of these hit classes, the 3-(oxazolo[4,5-b] pyridin-2-yl)anilides. Sharp SAR is revealed, with our most active compound (5) exhibiting an IC50 of 91 nM against the human pathogenic strain T.b. rhodesiense and being more than 700 times less toxic towards the L6 mammalian cell line. Physicochemical properties are attractive for many compounds in this series. For the most potent representatives, we show that solubility and metabolic stability are key parameters to target during future optimisation.[GRAPHICS](C) 2013 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2013.05.007