2-(2-fluoro-5-nitrophenyl)oxazolo[4,5-b]pyridine | 1533399-26-6

• 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-(2-fluoro-5-nitrophenyl)oxazolo[4,5-b]pyridine
• CAS: 1533399-26-6
• 化学式: C₁₂H₆FN₃O₃
• 分子量: 259.196
• InChiKey: QITMRUWUCROSKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.94
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.06
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-(2-fluoro-5-nitrophenyl)oxazolo[4,5-b]pyridine 在 tin(II) chloride dihdyrate 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 反应 11.03h， 生成 N-(4-fluoro-3-(oxazolo[4,5-b]pyridin-2-yl)phenyl)-N-methylfuran-2-carboxamide
  参考文献：
  名称：

  Substituted 2-Phenylimidazopyridines: A New Class of Drug Leads for Human African Trypanosomiasis

  摘要：

  A phenotypic screen of a compound library for antiparasitic activity on Trypanosoma brucei, the causative agent of human African trypanosomiasis, led to the identification of substituted 2-(3-aminophenyl)oxazolopyridines as a starting point for hit-to-lead medicinal chemistry. A total of 110 analogues were prepared, which led to the identification of 64, a substituted 2-(3-aminophenyl)imidazopyridine. This compound showed antiparasitic activity in vitro with an EC50 of 2 nM and displayed reasonable druglike properties when tested in a number of in vitro assays. The compound was orally bioavailable and displayed good plasma and brain exposure in mice. Compound 64 cured mice infected with Trypanosorna brucei when dosed orally down to 2.5 mg/kg. Given its potent antiparasitic properties and its ease of synthesis, compound 64 represents a new lead for the development of drugs to treat human African trypanosomiasis.

  DOI：

  10.1021/jm401178t
• 作为产物：
  描述：

  2-氨基-3-羟基吡啶 、 2-氟-5-硝基苯甲酸 在 polyphosphoric acid 作用下， 反应 5.0h， 以62.2%的产率得到2-(2-fluoro-5-nitrophenyl)oxazolo[4,5-b]pyridine
  参考文献：
  名称：

  Substituted 2-Phenylimidazopyridines: A New Class of Drug Leads for Human African Trypanosomiasis

  摘要：

  A phenotypic screen of a compound library for antiparasitic activity on Trypanosoma brucei, the causative agent of human African trypanosomiasis, led to the identification of substituted 2-(3-aminophenyl)oxazolopyridines as a starting point for hit-to-lead medicinal chemistry. A total of 110 analogues were prepared, which led to the identification of 64, a substituted 2-(3-aminophenyl)imidazopyridine. This compound showed antiparasitic activity in vitro with an EC50 of 2 nM and displayed reasonable druglike properties when tested in a number of in vitro assays. The compound was orally bioavailable and displayed good plasma and brain exposure in mice. Compound 64 cured mice infected with Trypanosorna brucei when dosed orally down to 2.5 mg/kg. Given its potent antiparasitic properties and its ease of synthesis, compound 64 represents a new lead for the development of drugs to treat human African trypanosomiasis.

  DOI：

  10.1021/jm401178t