N-(4,6-dimethylpyridin-2-yl)-4-acetoxy-3-methoxycinnamamide

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: N-(4,6-dimethylpyridin-2-yl)-4-acetoxy-3-methoxycinnamamide
• 英文别名: [4-[(E)-3-[(4,6-dimethylpyridin-2-yl)amino]-3-oxoprop-1-enyl]-2-methoxyphenyl] acetate
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: NHSYFRNFFRRVKA-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4,6-dimethylpyridin-2-yl)-4-acetoxy-3-methoxycinnamamide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以59%的产率得到(E)-N-(4,6-dimethylpyridin-2-yl)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enamide
  参考文献：
  名称：

  Non-acidic antiinflammatory compounds II. Synthesis and activity of 6-amino-2,4-lutidine derivatives

  摘要：

  Benzamides I, phenylalkanamides II and cinnamamides III are structurally related to the antiinflammatory N-(4,6-dimethylpyridin-2-yl)benzamide 1. These were synthesized and the transformation of the 2-aminopyridine nucleus of benzamides I into a 2-imino-1,2-dihydropyridine structure (compounds IV) was also carried out. Of the 49 new derivatives, the 3-fluorobenzamide 9 was the most potent in the oral treatment of carrageenen-induced peripheral edema; IC50 = 12.2 mg.kg(-1). It was 3 times as active as benzamide 1, but the latter nevertheless had a better therapeutic index (LD(50)/IC50) of 52 against 23. Benzamide 1, a non-acidic antiinflammatory compound devoid of any blocking activity on cyclooxygenase, markedly reduces the production of reactive oxygen species in rat peritoneal macrophages. This compound probably acts at the membrane, perhaps by interference with transmembrane events.

  DOI：

  10.1016/0223-5234(94)90107-4
• 作为产物：
  描述：

  阿魏酸 在 吡啶 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 N-(4,6-dimethylpyridin-2-yl)-4-acetoxy-3-methoxycinnamamide
  参考文献：
  名称：

  Non-acidic antiinflammatory compounds II. Synthesis and activity of 6-amino-2,4-lutidine derivatives

  摘要：

  Benzamides I, phenylalkanamides II and cinnamamides III are structurally related to the antiinflammatory N-(4,6-dimethylpyridin-2-yl)benzamide 1. These were synthesized and the transformation of the 2-aminopyridine nucleus of benzamides I into a 2-imino-1,2-dihydropyridine structure (compounds IV) was also carried out. Of the 49 new derivatives, the 3-fluorobenzamide 9 was the most potent in the oral treatment of carrageenen-induced peripheral edema; IC50 = 12.2 mg.kg(-1). It was 3 times as active as benzamide 1, but the latter nevertheless had a better therapeutic index (LD(50)/IC50) of 52 against 23. Benzamide 1, a non-acidic antiinflammatory compound devoid of any blocking activity on cyclooxygenase, markedly reduces the production of reactive oxygen species in rat peritoneal macrophages. This compound probably acts at the membrane, perhaps by interference with transmembrane events.

  DOI：

  10.1016/0223-5234(94)90107-4

文献信息

• Non-acidic antiinflammatory compounds II. Synthesis and activity of 6-amino-2,4-lutidine derivatives
  作者：J ROBERT、S ROBERTPIESSARD、M DUFLOS、G LEBAUT、E KHETTAB、N GRIMAUD、J PETIT、L WELIN

  DOI：10.1016/0223-5234(94)90107-4

  日期：——

  Benzamides I, phenylalkanamides II and cinnamamides III are structurally related to the antiinflammatory N-(4,6-dimethylpyridin-2-yl)benzamide 1. These were synthesized and the transformation of the 2-aminopyridine nucleus of benzamides I into a 2-imino-1,2-dihydropyridine structure (compounds IV) was also carried out. Of the 49 new derivatives, the 3-fluorobenzamide 9 was the most potent in the oral treatment of carrageenen-induced peripheral edema; IC50 = 12.2 mg.kg(-1). It was 3 times as active as benzamide 1, but the latter nevertheless had a better therapeutic index (LD(50)/IC50) of 52 against 23. Benzamide 1, a non-acidic antiinflammatory compound devoid of any blocking activity on cyclooxygenase, markedly reduces the production of reactive oxygen species in rat peritoneal macrophages. This compound probably acts at the membrane, perhaps by interference with transmembrane events.