2-(N-diisopropyl)amino-3-nitroimidazo[1,2-a]pyridine | 1281989-10-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2-(N-diisopropyl)amino-3-nitroimidazo[1,2-a]pyridine
• 英文别名: 3-nitro-N,N-di(propan-2-yl)imidazo[1,2-a]pyridin-2-amine
• CAS: 1281989-10-3
• 化学式: C₁₃H₁₈N₄O₂
• 分子量: 262.312
• InChiKey: TZOZJEJQUVZWOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二异丙胺 、 2-cyano-3-nitroimidazo[1,2-a]pyridine 反应 3.0h， 以56%的产率得到2-(N-diisopropyl)amino-3-nitroimidazo[1,2-a]pyridine
  参考文献：
  名称：

  Docking simulations, synthesis, and anti-inflammatory activity evaluation of 2-(N-alkyl)amino-3-nitroimidazo[1,2-a]pyridines

  摘要：

  A set of imidazo[1,2-a]pyridine derivatives was submitted to a docking analysis on COX-1 and COX-2. Although most of the compounds showed affinity for both COX-1 and COX-2, compound 1h showed a higher COX-1 affinity while 1i was more selective to COX-2. None of them had a dagger G value higher than indomethacin. Compounds 1b, 1c, and 1g were synthesized and evaluated as potential anti-inflammatory agents. Compound 2-(N-cyclopropyl)amino-3-nitroimidazo[1,2-a]pyridine (1c) which gave a very poor affinity for either COX-1 or COX-2, showed anti-inflammatory activity (20 mg/kg) on the cotton pellet granuloma bioassay, with no induction of gastrointestinal damage.

  DOI：

  10.1007/s00044-011-9585-5

文献信息

• Docking simulations, synthesis, and anti-inflammatory activity evaluation of 2-(N-alkyl)amino-3-nitroimidazo[1,2-a]pyridines
  作者：Yazmín K. Márquez-Flores、Ma. Elena Campos-Aldrete、Héctor Salgado-Zamora、José Correa-Basurto、Ma. Estela Meléndez-Camargo

  DOI：10.1007/s00044-011-9585-5

  日期：2012.6

  A set of imidazo[1,2-a]pyridine derivatives was submitted to a docking analysis on COX-1 and COX-2. Although most of the compounds showed affinity for both COX-1 and COX-2, compound 1h showed a higher COX-1 affinity while 1i was more selective to COX-2. None of them had a dagger G value higher than indomethacin. Compounds 1b, 1c, and 1g were synthesized and evaluated as potential anti-inflammatory agents. Compound 2-(N-cyclopropyl)amino-3-nitroimidazo[1,2-a]pyridine (1c) which gave a very poor affinity for either COX-1 or COX-2, showed anti-inflammatory activity (20 mg/kg) on the cotton pellet granuloma bioassay, with no induction of gastrointestinal damage.