N-benzyl-1-[4-(aminosulfonyl)phenyl]-5-phenyl-1H-1,2,4-triazole-3-carboxamide | 1620558-04-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-benzyl-1-[4-(aminosulfonyl)phenyl]-5-phenyl-1H-1,2,4-triazole-3-carboxamide
• 英文别名: N-benzyl-5-phenyl-1-(4-sulfamoylphenyl)-1,2,4-triazole-3-carboxamide
• CAS: 1620558-04-4
• 化学式: C₂₂H₁₉N₅O₃S
• 分子量: 433.491
• InChiKey: VPQXDAWTQZSNTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-苯基-5-噁唑酮 在 盐酸 、 sodium nitrite 作用下， 以 甲醇 、 水 为溶剂， 反应 5.25h， 生成 N-benzyl-1-[4-(aminosulfonyl)phenyl]-5-phenyl-1H-1,2,4-triazole-3-carboxamide
  参考文献：
  名称：

  Novel 1-[4-(Aminosulfonyl)phenyl]-1H-1,2,4-triazole derivatives with remarkable selective COX-2 inhibition: Design, synthesis, molecular docking, anti-inflammatory and ulcerogenicity studies

  摘要：

  A novel series of 1,2,4-triazole derivatives were synthesized and confirmed with different spectroscopic techniques. The prepared compounds exhibited remarkable anti-inflammatory activity comparable to that of indomethacin and celecoxib after 3 h. The tested compounds exhibited very low incidence of gastric ulceration compared to indomethacin. Most of the newly developed compounds showed excellent selectivity towards human COX-2 with selectivity indices (COX-1 IC50/COX-2 IC50) ranged from 62.5 to 2127. Docking studies results revealed that the highly selective tested compounds 6h and 6j showed lower CDOCKER energies, which means that they require less energy for proper interaction with the enzyme. The additional H-bonds with the oxygen of the amide and/or H of NH of the amide with the amino acid residues may be responsible for the higher binding affinity of this group of compounds towards COX-2.

  DOI：

  10.1016/j.ejmech.2014.06.049