N-benzyl-2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetamide | 405279-26-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-benzyl-2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetamide
• 英文别名: N-benzyl-2-(2-methyl-4-nitroimidazol-1-yl)acetamide
• CAS: 405279-26-7
• 化学式: C₁₃H₁₄N₄O₃
• mdl: MFCD02745949
• 分子量: 274.279
• InChiKey: ANDXGHGQPGMSAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲基-4-硝基咪唑 、 N-苄基-2-氯乙酰胺 在 氢氧化钾 作用下， 以 乙腈 为溶剂， 反应 8.5h， 以83.9%的产率得到N-benzyl-2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetamide
  参考文献：
  名称：

  Synthesis and in vitro trichomonicidal, giardicidal and amebicidal activity of N-acetamide(sulfonamide)-2-methyl-4-nitro-1H-imidazoles☆

  摘要：

  Two new series of imidazole derivatives (acetamides: 1-8 and sulfonamides: 9-15) were synthesized using a short synthetic route. Compound 1 as well as the intermediate 16g were characterized by X-ray crystallography. Imidazole derivatives 1-15 were tested in vitro against three unicellular parasites (Giardia intestinalis, Trichomonas vaginalis and Entamoeba histolytica) in comparison with benznidazole (Bzn) and metronidazole. Compound 1 [N-benzyl-2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetamide] was 2 times more active than Bzn against T vaginalis and G. intestinalis and it was as active as Bzn against E. histolytica. Sulfonamides showed selective toxicity against E. histolytica over the other parasites. Toxicity assay showed that all compounds are non-cytotoxic against MDCK cell line. The results revealed that compounds 1-15 have antiparasitic bioactivity in the micromolar range against the parasites tested, and could be considered as benznidazole bioisosteres. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.005

文献信息

• Synthesis and in vitro trichomonicidal, giardicidal and amebicidal activity of N-acetamide(sulfonamide)-2-methyl-4-nitro-1H-imidazoles☆
  作者：Emanuel Hernández-Núñez、Hugo Tlahuext、Rosa Moo-Puc、Héctor Torres-Gómez、Reyna Reyes-Martínez、Roberto Cedillo-Rivera、Carlos Nava-Zuazo、Gabriel Navarrete-Vazquez

  DOI：10.1016/j.ejmech.2009.01.005

  日期：2009.7

  Two new series of imidazole derivatives (acetamides: 1-8 and sulfonamides: 9-15) were synthesized using a short synthetic route. Compound 1 as well as the intermediate 16g were characterized by X-ray crystallography. Imidazole derivatives 1-15 were tested in vitro against three unicellular parasites (Giardia intestinalis, Trichomonas vaginalis and Entamoeba histolytica) in comparison with benznidazole (Bzn) and metronidazole. Compound 1 [N-benzyl-2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetamide] was 2 times more active than Bzn against T vaginalis and G. intestinalis and it was as active as Bzn against E. histolytica. Sulfonamides showed selective toxicity against E. histolytica over the other parasites. Toxicity assay showed that all compounds are non-cytotoxic against MDCK cell line. The results revealed that compounds 1-15 have antiparasitic bioactivity in the micromolar range against the parasites tested, and could be considered as benznidazole bioisosteres. (C) 2009 Elsevier Masson SAS. All rights reserved.