5-benzo[1,3]dioxol-5-yl-penta-2,4-dienoic acid 1-(3-nitrophenyl)-1H-[1,2,3]triazol-4-ylmethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-benzo[1,3]dioxol-5-yl-penta-2,4-dienoic acid 1-(3-nitrophenyl)-1H-[1,2,3]triazol-4-ylmethyl ester
• 英文别名: [1-(3-nitrophenyl)triazol-4-yl]methyl (2E,4E)-5-(1,3-benzodioxol-5-yl)penta-2,4-dienoate
• 化学式: C₂₁H₁₆N₄O₆
• 分子量: 420.381
• InChiKey: FSXRZRHFOJUMAG-BQJQTIKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  胡椒碱 在 甲醇 、 caesium carbonate 、 copper(II) sulfate 、 sodium ascorbate 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 84.0h， 生成 5-benzo[1,3]dioxol-5-yl-penta-2,4-dienoic acid 1-(3-nitrophenyl)-1H-[1,2,3]triazol-4-ylmethyl ester
  参考文献：
  名称：

  Design, synthesis and biological evaluation of piperic acid triazolyl derivatives as potent anti-inflammatory agents

  摘要：

  Nineteen novel piperine based triazoles have been synthesized using click chemistry approach and were tested for in vivo anti-inflammatory activity. The most active compounds were evaluated for in vitro TNF-alpha expression. Compounds 3g and 3f were found to show significant in vivo inhibition of inflammation, 80.40% and 76.71%, respectively after 5 h in comparison to piperine (54.72%) and the standard drug indomethacin (77.02%) without causing any damage to the stomach. Compounds 3g and 3f suppressed TNF-a level by 73.73% and 70.64%, respectively and protein expression of COX-2, NF-kappa B and TNF-alpha more than indomethacin. Moreover, the compound 3g was found to show significant analgesic activity of 54.09% which was comparable with the indomethacin (57.43%). (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.001