2-(5-(4-nitrobenzylthio)-4-phenyl-4H-1,2,4-triazol-3-yl)-6-bromo-imidazo[1,2-a]pyridine | 1516888-40-6

• 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-(5-(4-nitrobenzylthio)-4-phenyl-4H-1,2,4-triazol-3-yl)-6-bromo-imidazo[1,2-a]pyridine
• CAS: 1516888-40-6
• 化学式: C₂₂H₁₅BrN₆O₂S
• 分子量: 507.37
• InChiKey: OQIYZCXRIMYZGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.55
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  91.15
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  2-氨基-5-溴吡啶 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 2-(5-(4-nitrobenzylthio)-4-phenyl-4H-1,2,4-triazol-3-yl)-6-bromo-imidazo[1,2-a]pyridine
  参考文献：
  名称：

  New 6-bromoimidazo[1,2-a]pyridine-2-carbohydrazide derivatives: synthesis and anticonvulsant studies

  摘要：

  In the present work, we report the facile synthesis and anticonvulsant study of new imidazo[1,2-a]pyridines carrying biologically active hydrazone functionality (3a-3e) and suitably substituted 1,2,4-triazole moieties (4, 5a-5d, 6, and 7a-7d). The newly synthesized intermediates and final compounds were characterized by various spectral techniques such as FTIR, H-1 NMR, C-13 NMR, and mass spectral and elemental analysis studies. The in vivo anticonvulsant study of the target compounds were carried out following maximal electroshock seizure and subcutaneous pentylene tetrazole methods, while their toxicity study was performed following rotarod method by taking 20, 40, and 100 mg/kg dose levels. Most of the new compounds displayed remarkable anticonvulsant properties at these doses. Particularly, compounds 3b and 4 carrying hydrogen bond donor groups, viz. hydroxyl and amine moieties respectively, exhibited complete protection against seizure and their results are comparable to that of standard drug diazepam. Further, the motor impairment study revealed that all the compounds are nontoxic upto 100 mg/kg.

  DOI：

  10.1007/s00044-013-0887-7