4-(pyridin-2-yl)-1,3-oxazol-2-amine | 1014629-84-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(pyridin-2-yl)-1,3-oxazol-2-amine
• 英文别名: 4-(2-Pyridinyl)-2-oxazolamine；4-pyridin-2-yl-1,3-oxazol-2-amine
• CAS: 1014629-84-5
• 化学式: C₈H₇N₃O
• 分子量: 161.163
• InChiKey: OHXVGLQBMNCUJR-UHFFFAOYSA-N

物化性质

• 沸点：
  362.4±34.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(pyridin-2-yl)-1,3-oxazol-2-amine 、 苯甲酰氯 在 N-甲基咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以65%的产率得到2-[(benzoyl)amino]-4-(pyridin-2-yl)oxazole
  参考文献：
  名称：

  Structure–activity relationships of 2-aminothiazoles effective against Mycobacterium tuberculosis

  摘要：

  A series of 2-aminothiazoles was synthesized based on a HTS scaffold from a whole-cell screen against Mycobacterium tuberculosis (Mtb). The SAR shows the central thiazole moiety and the 2-pyridyl moiety at C-4 of the thiazole are intolerant to modification. However, the N-2 position of the aminothiazole exhibits high flexibility and we successfully improved the antitubercular activity of the initial hit by more than 128-fold through introduction of substituted benzoyl groups at this position. N-(3-Chlorobenzoyl)-4-(2-pyridinyl)-1,3-thiazol-2-amine (55) emerged as one of the most promising analogues with a MIC of 0.024 mu M or 0.008 mu g/mL in 7H9 media and therapeutic index of nearly similar to 300. However, 55 is rapidly metabolized by human liver microsomes (t(1/2) = 28 min) with metabolism occurring at the invariant aminothiazole moiety and Mtb develops spontaneous low-level resistance with a frequency of similar to 10 (5). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.048
• 作为产物：
  描述：

  2-氧代-2-(吡啶-2-基)乙酸乙酯 在 盐酸 、 水 作用下， 以 乙醇 、 水 为溶剂， 反应 15.5h， 生成 4-(pyridin-2-yl)-1,3-oxazol-2-amine
  参考文献：
  名称：

  Structure–activity relationships of 2-aminothiazoles effective against Mycobacterium tuberculosis

  摘要：

  A series of 2-aminothiazoles was synthesized based on a HTS scaffold from a whole-cell screen against Mycobacterium tuberculosis (Mtb). The SAR shows the central thiazole moiety and the 2-pyridyl moiety at C-4 of the thiazole are intolerant to modification. However, the N-2 position of the aminothiazole exhibits high flexibility and we successfully improved the antitubercular activity of the initial hit by more than 128-fold through introduction of substituted benzoyl groups at this position. N-(3-Chlorobenzoyl)-4-(2-pyridinyl)-1,3-thiazol-2-amine (55) emerged as one of the most promising analogues with a MIC of 0.024 mu M or 0.008 mu g/mL in 7H9 media and therapeutic index of nearly similar to 300. However, 55 is rapidly metabolized by human liver microsomes (t(1/2) = 28 min) with metabolism occurring at the invariant aminothiazole moiety and Mtb develops spontaneous low-level resistance with a frequency of similar to 10 (5). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.048

文献信息

• 取代的1,3-杂唑类化合物、其制备方法、包含 其的药物组合物及用途
  申请人：中国医学科学院医药生物技术研究所

  公开号：CN105820163B

  公开（公告）日：2019-02-22

  取代的1,3‑杂唑类化合物、其制备方法、包含其的药物组合物及用途。本发明涉及式I的化合物，或其药学上可接受的盐、立体异构体或溶剂化物，其中R1、R2、R3和X如本文中所定义；其制备方法、包含其的药物组合物及其用途。本发明的化合物是一类新型抗结核化合物，其不仅对结核杆菌敏感株有效，而且还对于对异烟肼和利福平等传统一线抗结核药物有耐药性的耐药菌株有效，并且对结核分枝杆菌具有良好的选择性。
• FAAH INHIBITORS
  申请人：Sprott Kevin

  公开号：US20090118503A1

  公开（公告）日：2009-05-07

  Indole derivatives that are useful for treating pain, inflammation and other conditions are described. Certain of the compounds are benzyl derivatives and others are benzoyl derivatives. The compounds are substituted at least at the 3 position of the indole.

  本文描述了可用于治疗疼痛、炎症和其他病症的吲哚衍生物。其中某些化合物是苄基衍生物，而其他化合物是苯甲酰基衍生物。这些化合物至少在吲哚的3位被取代。
• USEFUL INDOLE COMPOUNDS
  申请人：Bartolini Wilmin

  公开号：US20090264653A1

  公开（公告）日：2009-10-22

  Indoles that have activity as inhibitors of FAAH are described as are indoles and indole derivatives that have activity as inhibitors of DAO.

  本文描述了具有FAAH抑制剂活性的吲哚化合物，以及具有DAO抑制剂活性的吲哚及其衍生物。
• INDOLE COMPOUNDS
  申请人：Talley John Jeffrey

  公开号：US20100197708A1

  公开（公告）日：2010-08-05

  Indole derivatives that are useful for treating pain, inflammation and other conditions are described. Certain of the compounds are benzyl derivatives and others are benzoyl derivatives. The compounds are substituted at least at the 3 position of the indole.

  本文介绍了用于治疗疼痛、炎症和其他疾病的吲哚衍生物。其中某些化合物是苄基衍生物，而其他化合物是苯甲酰基衍生物。这些化合物至少在吲哚的3位被取代。
• SUBSTITUTED AMINOTHIAZOLES FOR THE TREATMENT OF TUBERCULOSIS
  申请人：THE BROAD INSTITUTE, INC.

  公开号：US20160031874A1

  公开（公告）日：2016-02-04

  Disclosed are substituted aminothiazoles, which can be used for, among other things, the treatment of tuberculosis, pharmaceutical compositions containing the same, and methods of using the same.

  本发明涉及一种取代氨基噻唑，可用于治疗结核病等，包含该化合物的制药组合物，以及使用该化合物的方法。