1-(4-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1H-[1,2,4]triazole-3-carboxylic acid ethylamide | 1598427-91-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1H-[1,2,4]triazole-3-carboxylic acid ethylamide
• 英文别名: N-ethyl-1-(4-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1,2,4-triazole-3-carboxamide
• CAS: 1598427-91-8
• 化学式: C₂₁H₂₄N₄O₅
• 分子量: 412.445
• InChiKey: PMGHNASNVFZIBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  96.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (3,4,5-三甲氧基苯甲酰基)氨基]乙酸 在 盐酸 、 乙酸酐 、 sodium nitrite 作用下， 以 甲醇 、 水 为溶剂， 反应 2.67h， 生成 1-(4-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1H-[1,2,4]triazole-3-carboxylic acid ethylamide
  参考文献：
  名称：

  1-(4-Methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazole-3-carboxamides: Synthesis, molecular modeling, evaluation of their anti-inflammatory activity and ulcerogenicity

  摘要：

  A series of novel 1-(4-methoxyphenyl)-5-(3,4,5-trimethoxyphenyl)-1H-1,2,4-triazole-3-carboxamides were synthesized and confirmed with different spectroscopic techniques. The prepared compounds exhibited remarkable anti-inflammatory activity that represents 38%-100% of indomethacin activity and 44%-115% of celecoxib activity after 3 h. The anilides 5a-1 and hydrazide 6 exhibit low incidence of gastric ulceration compared to indomethacin which was confirmed with histopathological investigation. In vitro COX-1/COX-2 inhibition studies showed compounds 4b (COX-1 IC50 = 45.9 mu M; COX-2 IC50 = 68.2 mu M) and 6 (COX-1 IC50 = 39.8 mu M; COX-2 IC50 = 46.3 mu M) are the most potent COX inhibitors in the tested compounds. The binding mode for some of the tested compounds to the enzymes was predicted using docking studies. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.001