3-[5-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethylsulfanyl]-4-phenyl-4H-[1,2,4]triazol-3-yl]pyridine | 1234796-40-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-[5-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethylsulfanyl]-4-phenyl-4H-[1,2,4]triazol-3-yl]pyridine
• 英文别名: 3-[5-[2-(2-methyl-5-nitroimidazol-1-yl)ethylsulfanyl]-4-phenyl-1,2,4-triazol-3-yl]pyridine
• CAS: 1234796-40-7
• 化学式: C₁₉H₁₇N₇O₂S
• 分子量: 407.456
• InChiKey: CLYKQJRMFZJQNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  133
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-methylbenzenesulfonate 、 4-苯基-5-吡啶-3-基-4H-[1,2,4]三唑 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以27%的产率得到3-[5-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethylsulfanyl]-4-phenyl-4H-[1,2,4]triazol-3-yl]pyridine
  参考文献：
  名称：

  Synthesis and antimicrobial activity of new 1,2,4-triazole-3-thiol metronidazole derivatives

  摘要：

  New 1,2,4-triazole-3-thiol metronidazole derivatives have been synthesized by treating 1,2,4-triazole-3-thiols with metronidazole tosylate (toluene-4-sulfonic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester) in DMF and in the presence of potassium carbonate as a base. S-alkylated and N-alkylated products were obtained, with the S-alkylated being the major products. All of the newly synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR, and high-resolution mass spectrometry. The antiparasitic activity of the compounds against Entamoeba histolytica and Giardia intestinalis was investigated. The antibacterial and antifungal activity of the compounds, assessed as minimal inhibitory concentration, was also investigated.

  DOI：

  10.1007/s00706-010-0281-9

文献信息

• Synthesis and antimicrobial activity of new 1,2,4-triazole-3-thiol metronidazole derivatives
  作者：Haythem A. Saadeh、Ibrahim M. Mosleh、Amal G. Al-Bakri、Mohammad S. Mubarak

  DOI：10.1007/s00706-010-0281-9

  日期：2010.4

  New 1,2,4-triazole-3-thiol metronidazole derivatives have been synthesized by treating 1,2,4-triazole-3-thiols with metronidazole tosylate (toluene-4-sulfonic acid 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl ester) in DMF and in the presence of potassium carbonate as a base. S-alkylated and N-alkylated products were obtained, with the S-alkylated being the major products. All of the newly synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR, and high-resolution mass spectrometry. The antiparasitic activity of the compounds against Entamoeba histolytica and Giardia intestinalis was investigated. The antibacterial and antifungal activity of the compounds, assessed as minimal inhibitory concentration, was also investigated.