N-(3,5-diiodo-4-methoxyphenethyl)-benzamide | 1186434-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3,5-diiodo-4-methoxyphenethyl)-benzamide
• 英文别名: N-[2-(3,5-diiodo-4-methoxyphenyl)ethyl]benzamide
• CAS: 1186434-74-1
• 化学式: C₁₆H₁₅I₂NO₂
• 分子量: 507.11
• InChiKey: XZYWUGRSKVQSGH-UHFFFAOYSA-N

物化性质

• 沸点：
  602.3±55.0 °C(predicted)
• 密度：
  1.843±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-Boc-酪胺 在 盐酸 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 potassium carbonate 、 N,N'-二异丙基碳二亚胺 作用下， 以 甲醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 87.0h， 生成 N-(3,5-diiodo-4-methoxyphenethyl)-benzamide
  参考文献：
  名称：

  Anti-Parasite Activity of Novel 3,5-Diiodophenethyl-benzamides

  摘要：

  Novel iodotyramides with para-substituted benzoic acids were synthesized via electrophilic aromatic substitutions and amide coupling via N,N'-diisopropylcarbodiimide (DIC) in dimethylformamide (DMF). All derivatives were in vitro screened against U-937 macrophages and Plasmodium faleiparum, Leishmania panamensis and Trypanosoma cruzi protozoan parasites. The hemolytic activity was evaluated on human red blood cells (RBC). Compounds N-(4-hydroxy-3,5-diiodophenethyl)-4-methylbenzamide and N-(3,5-diiodo-4-methoxyphenethyl)-4-methoxybenzamide were the most active against L. panamensis with an effective concentration 50 (EC50) of 17.9 and 17.5 mu g mL(-1), respectively; while compounds N-(3,5-diiodo-4-methoxyphenethyl)-4-mcthylbenzamide and N-(3,5-diiodo-4-methoxyphcnethyl)-4-methoxybenzamide were the most active for T. cruzi with EC50 values of 23.75 and 6.19 mu g mL(-1), respectively. In contrast, all derivatives showed high activity against P. falciparum with EC50 < 25 mu g mL(-1), except compound N-(4-hydroxy-3,5-diiodophenethyl)-benzamide. No compound was hemolytic over RBC. This report represents the importance of novel iodotyramides as anti-parasites agents.

  DOI：

  10.21577/0103-5053.20180160

文献信息

• Anti-Parasite Activity of Novel 3,5-Diiodophenethyl-benzamides
  作者：Manuel Pastrana Restrepo、Verónica Surmay Surmay、Elkin Galeano Jaramillo、Sara Robledo Restrepo

  DOI：10.21577/0103-5053.20180160

  日期：——

  Novel iodotyramides with para-substituted benzoic acids were synthesized via electrophilic aromatic substitutions and amide coupling via N,N'-diisopropylcarbodiimide (DIC) in dimethylformamide (DMF). All derivatives were in vitro screened against U-937 macrophages and Plasmodium faleiparum, Leishmania panamensis and Trypanosoma cruzi protozoan parasites. The hemolytic activity was evaluated on human red blood cells (RBC). Compounds N-(4-hydroxy-3,5-diiodophenethyl)-4-methylbenzamide and N-(3,5-diiodo-4-methoxyphenethyl)-4-methoxybenzamide were the most active against L. panamensis with an effective concentration 50 (EC50) of 17.9 and 17.5 mu g mL(-1), respectively; while compounds N-(3,5-diiodo-4-methoxyphenethyl)-4-mcthylbenzamide and N-(3,5-diiodo-4-methoxyphcnethyl)-4-methoxybenzamide were the most active for T. cruzi with EC50 values of 23.75 and 6.19 mu g mL(-1), respectively. In contrast, all derivatives showed high activity against P. falciparum with EC50 < 25 mu g mL(-1), except compound N-(4-hydroxy-3,5-diiodophenethyl)-benzamide. No compound was hemolytic over RBC. This report represents the importance of novel iodotyramides as anti-parasites agents.