N-(4-acetylphenyl)-2-(1H-indol-3-yl)acetamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-acetylphenyl)-2-(1H-indol-3-yl)acetamide
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: LZQWBBCCVQWFEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  62
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  硫脲 、 N-(4-acetylphenyl)-2-(1H-indol-3-yl)acetamide 在 碘 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以35%的产率得到N-[4-(2-Amino-4,5-dihydro-thiazol-4-yl)-phenyl]-2-(1H-indol-3-yl)-acetamide
  参考文献：
  名称：

  Antiinflammatory activity of novel indole derivatives

  摘要：

  3-[(2-Imidazolyl, benzimidazolyl or benzoxazolyl)alkyl]indoles 2a-h were synthesized by cyclizing the carboxylic group of (3-indolyl)alkanoic acids 1 with ethylenediamine, o-phenylenediamine or o-aminophenol, respectively. Reaction of 1 with p-aminoacetophenone or aryl-substituted thiosemicarbazones yielded N-(4-acetylphenyl)-(2 or 4)-(indol-3-yl)alkylcarboxamides 3a-b or l-arylidene 4-[2-(indol-3-yl)(acetyl or propionyl)]thiosemicarbazides 5a-h; 3a-b were cyclized into N-[4-(2-aminothiazol-4-yl)phenyl]-(2 or 4)-(indol-3-yl)alkylcarboxamides 4a-b. Cyclization of 5a-h with malonic acid yielded 1-[2-(indol-3-yl)(acetyl or propionyl)]-3-arylideneamino-2-thiobarbituric acids 6a-h, which were finally converted into corresponding Mannich bases 7a-f. Compounds 2a-h, 4a-b, 6a-h and 7a-f were evaluated for their antiinflammatory activity. Compounds 2e, 2g, 4b, 6c and 6d exhibited promising antiinflammatory activity with a lower ulcerogenic liability than indomethacin.

  DOI：

  10.1016/0223-5234(94)90193-7
• 作为产物：
  描述：

  3-吲哚乙酸 、 4-氨基苯乙酮 在 N,N'-二环己基碳二亚胺 作用下， 以 乙酸乙酯 为溶剂， 反应 10.0h， 以60%的产率得到N-(4-acetylphenyl)-2-(1H-indol-3-yl)acetamide
  参考文献：
  名称：

  Antiinflammatory activity of novel indole derivatives

  摘要：

  3-[(2-Imidazolyl, benzimidazolyl or benzoxazolyl)alkyl]indoles 2a-h were synthesized by cyclizing the carboxylic group of (3-indolyl)alkanoic acids 1 with ethylenediamine, o-phenylenediamine or o-aminophenol, respectively. Reaction of 1 with p-aminoacetophenone or aryl-substituted thiosemicarbazones yielded N-(4-acetylphenyl)-(2 or 4)-(indol-3-yl)alkylcarboxamides 3a-b or l-arylidene 4-[2-(indol-3-yl)(acetyl or propionyl)]thiosemicarbazides 5a-h; 3a-b were cyclized into N-[4-(2-aminothiazol-4-yl)phenyl]-(2 or 4)-(indol-3-yl)alkylcarboxamides 4a-b. Cyclization of 5a-h with malonic acid yielded 1-[2-(indol-3-yl)(acetyl or propionyl)]-3-arylideneamino-2-thiobarbituric acids 6a-h, which were finally converted into corresponding Mannich bases 7a-f. Compounds 2a-h, 4a-b, 6a-h and 7a-f were evaluated for their antiinflammatory activity. Compounds 2e, 2g, 4b, 6c and 6d exhibited promising antiinflammatory activity with a lower ulcerogenic liability than indomethacin.

  DOI：

  10.1016/0223-5234(94)90193-7