N-[4-(2-氨基-4,5-二氢-1,3-噻唑-4-基)苯基]-4-(1H-吲哚-3-基)丁酰胺 | 161806-43-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: N-[4-(2-氨基-4,5-二氢-1,3-噻唑-4-基)苯基]-4-(1H-吲哚-3-基)丁酰胺
• 英文名称: N-[4-(2-Amino-4,5-dihydro-thiazol-4-yl)-phenyl]-4-(1H-indol-3-yl)-butyramide
• 英文别名: N-(4-(2-Amino-4,5-dihydro-4-thiazolyl)phenyl)-1H-indole-3-butanamide；N-[4-(2-amino-4,5-dihydro-1,3-thiazol-4-yl)phenyl]-4-(1H-indol-3-yl)butanamide
• CAS: 161806-43-5
• 化学式: C₂₁H₂₂N₄OS
• 分子量: 378.498
• InChiKey: LDBRTKUVBPJCHD-UHFFFAOYSA-N

物化性质

• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  109
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  硫脲 、 N-(4-Acetyl-phenyl)-4-(1H-indol-3-yl)-butyramide 在 碘 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以40%的产率得到N-[4-(2-氨基-4,5-二氢-1,3-噻唑-4-基)苯基]-4-(1H-吲哚-3-基)丁酰胺
  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

文献信息

• Antiinflammatory activity of novel indole derivatives
  作者：M Verma、M Tripathi、AK Saxena、K Shanker

  DOI：10.1016/0223-5234(94)90193-7

  日期：1994.1

  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.