2-methyl-5-(oxazolo[4,5-b]pyridin-2-yl)aniline | 313701-56-3

• 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-5-(oxazolo[4,5-b]pyridin-2-yl)aniline
• 英文别名: 2-Methyl-5-oxazolo[4,5-b]pyridin-2-yl-phenylamine；2-methyl-5-([1,3]oxazolo[4,5-b]pyridin-2-yl)aniline
• CAS: 313701-56-3
• 化学式: C₁₃H₁₁N₃O
• mdl: MFCD02084933
• 分子量: 225.25
• InChiKey: WGTVXCWMSWDXMG-UHFFFAOYSA-N

物化性质

• 溶解度：
  >33.8 [ug/mL]

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-5-(oxazolo[4,5-b]pyridin-2-yl)aniline 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以54%的产率得到N-(2-methyl-5-(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 、 3-氨基-4-甲基苯甲酸 在 polyphosphoric acid 作用下， 反应 4.0h， 以34%的产率得到2-methyl-5-(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

文献信息

• Antitrypanosomal Chloronitrobenzamides
  作者：Angela K. Carrillo、Tara Man Kadayat、Jong Yeon Hwang、Yizhe Chen、Fangyi Zhu、Gloria Holbrook、Kirsten Gillingwater、Michele C. Connelly、Lei Yang、Marcel Kaiser、R. Kiplin Guy

  DOI：10.1021/acs.jmedchem.3c01680

  日期：2024.3.14

  disease caused by Trypanosoma brucei gambiense (Tbg) or Trypanosoma brucei rhodesiense (Tbr), remains a significant public health concern with over 55 million people at risk of infection. Current treatments for HAT face the challenges of poor efficacy, drug resistance, and toxicity. This study presents the synthesis and evaluation of chloronitrobenzamides (CNBs) against Trypanosoma species, identifying

  非洲人类锥虫病 (HAT) 是一种被忽视的热带疾病，由布氏冈比亚锥虫( Tbg ) 或罗得西亚布氏锥虫( Tbr ) 引起，仍然是一个重大的公共卫生问题，超过 5500 万人面临感染风险。目前HAT的治疗面临着疗效差、耐药性和毒性的挑战。本研究介绍了针对锥虫物种的氯硝基苯甲酰胺 (CNB) 的合成和评估，鉴定了先前报道的化合物52作为一种有效的、选择性的口服生物可利用的抗锥虫药物。 52在体内具有良好的耐受性，并表现出良好的口服药代动力学，在 24 小时内维持超过细胞 EC 50 的血浆浓度，并且在单次口服给药（50 mg/kg）后在啮齿类动物中达到超过 7 μM 的峰值脑浓度。 52治疗显着延长了感染刚果锥虫和罗得西亚锥虫的小鼠的寿命。这些结果表明， 52是一种强效抗锥虫先导药物，具有开发治疗人类和动物非洲锥虫病的潜力。