1-methyl-2-(4-nitrobenzoyl)imidazole-5-carboxylic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methyl-2-(4-nitrobenzoyl)imidazole-5-carboxylic acid
• 英文别名: 3-Methyl-2-(4-nitrobenzoyl)imidazole-4-carboxylic acid
• 化学式: C₁₂H₉N₃O₅
• 分子量: 275.221
• InChiKey: IXYQRRCYNALKLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-methyl-2-(4-nitrobenzoyl)imidazolecarboxylate 在 硫酸 作用下， 反应 3.0h， 以84%的产率得到1-methyl-2-(4-nitrobenzoyl)imidazole-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and antiinflammatory—analgesic profile of 1-methyl-2-(4-X-benzoyl) imidazole-5-carboxylic acids

  摘要：

  A set of 1-methyl-2-(4-X-benzoyl)imidazole-5-carboxylic acids, designed as antiinflammatory-analgesic agents, were synthesized and biologically evaluated in vivo (writhing test and the carrageenen rat pleurisy) using tolmetin as a reference drug. The compounds were also tested in vitro on the cyclooxygenase enzyme of sheep vescicular microsome. Distribution coefficients In the octanol-buffer system at different pH values have been determined for their potential influence on activity. Although the investigated compounds exhibited moderate or no inhibitory activity against cyclooxygenase in in vitro and in vivo assays, two of them (the 4-nitrobenzoyl and the 4-chlorobenzoyl derivatives 1e and 1b) were found to be more active than tolmetin in the writhing test. Moreover, 1b also showed higher activity in the pleurisy assay.

  DOI：

  10.1016/0223-5234(96)88239-0

文献信息

• Caliendo G., Cirino G., Greco G., Novellino E., Perissutti E., Pinto A., +, Eur. J. Med. Chem., 30 (1995) N 4, S 315-320
  作者：Caliendo G., Cirino G., Greco G., Novellino E., Perissutti E., Pinto A., +

  DOI：——

  日期：——
• Synthesis and antiinflammatory—analgesic profile of 1-methyl-2-(4-X-benzoyl) imidazole-5-carboxylic acids
  作者：G Caliendo、G Cirino、G Greco、E Novellino、E Perissutti、A Pinto、V Santagada、L Sorrentino

  DOI：10.1016/0223-5234(96)88239-0

  日期：1995.1

  A set of 1-methyl-2-(4-X-benzoyl)imidazole-5-carboxylic acids, designed as antiinflammatory-analgesic agents, were synthesized and biologically evaluated in vivo (writhing test and the carrageenen rat pleurisy) using tolmetin as a reference drug. The compounds were also tested in vitro on the cyclooxygenase enzyme of sheep vescicular microsome. Distribution coefficients In the octanol-buffer system at different pH values have been determined for their potential influence on activity. Although the investigated compounds exhibited moderate or no inhibitory activity against cyclooxygenase in in vitro and in vivo assays, two of them (the 4-nitrobenzoyl and the 4-chlorobenzoyl derivatives 1e and 1b) were found to be more active than tolmetin in the writhing test. Moreover, 1b also showed higher activity in the pleurisy assay.