1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)-4-(aminomethyl)-1H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)-4-(aminomethyl)-1H-1,2,3-triazole
• 英文别名: [1-[2-(2-Methyl-5-nitroimidazol-1-yl)ethyl]triazol-4-yl]methanamine
• 化学式: C₉H₁₃N₇O₂
• mdl: MFCD17927606
• 分子量: 251.248
• InChiKey: JFPVGOWGRHRIEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)-4-(aminomethyl)-1H-1,2,3-triazole 、 三氟乙酸 以 水 、 乙腈 为溶剂， 生成 1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)-4-(aminomethyl)-1H-1,2,3-triazole trifluoroacetate salt
  参考文献：
  名称：

  Metronidazole-triazole conjugates: Activity against Clostridium difficile and parasites

  摘要：

  Metronidazole has been used clinically for over 50 years as an antiparasitic and broad-spectrum antibacterial agent effective against anaerobic bacteria. However resistance to metronidazole in parasites and bacteria has been reported, and improved second-generation metronidazole analogues are needed. The copper catalysed Huigsen azide-alkyne 1,3-dipolar cycloaddition offers a way to efficiently assemble new libraries of metronidazole analogues. Several new metronidazole-triazole conjugates (Mtz-triazoles) have been identified with excellent broad spectrum antimicrobial and antiparasitic activity targeting Clostridium difficile, Entamoeba histolytica and Giardia lambda. Cross resistance to metronidazole was observed against stable metronidazole resistant C. difficile and G.. lamblia strains. However for the most potent Mtz-triazoles, the activity remained in a therapeutically relevant window. (C) 2015 The Authors. Published by Elsevier Masson SAS. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).

  DOI：

  10.1016/j.ejmech.2015.06.019
• 作为产物：
  描述：

  甲硝唑 在 sodium azide 、 copper(II) sulfate 、 sodium ascorbate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.33h， 生成 1-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl)-4-(aminomethyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Metronidazole-triazole conjugates: Activity against Clostridium difficile and parasites

  摘要：

  Metronidazole has been used clinically for over 50 years as an antiparasitic and broad-spectrum antibacterial agent effective against anaerobic bacteria. However resistance to metronidazole in parasites and bacteria has been reported, and improved second-generation metronidazole analogues are needed. The copper catalysed Huigsen azide-alkyne 1,3-dipolar cycloaddition offers a way to efficiently assemble new libraries of metronidazole analogues. Several new metronidazole-triazole conjugates (Mtz-triazoles) have been identified with excellent broad spectrum antimicrobial and antiparasitic activity targeting Clostridium difficile, Entamoeba histolytica and Giardia lambda. Cross resistance to metronidazole was observed against stable metronidazole resistant C. difficile and G.. lamblia strains. However for the most potent Mtz-triazoles, the activity remained in a therapeutically relevant window. (C) 2015 The Authors. Published by Elsevier Masson SAS. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).

  DOI：

  10.1016/j.ejmech.2015.06.019