2-(2-hydroxy-3-nitrophenyl)-5-(1-methyl-4-nitro-1H-pyrrol-2-yl)-1,3,4-oxadiazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(2-hydroxy-3-nitrophenyl)-5-(1-methyl-4-nitro-1H-pyrrol-2-yl)-1,3,4-oxadiazole
• 英文别名: 2-[5-(1-Methyl-4-nitropyrrol-2-yl)-1,3,4-oxadiazol-2-yl]-6-nitrophenol；2-[5-(1-methyl-4-nitropyrrol-2-yl)-1,3,4-oxadiazol-2-yl]-6-nitrophenol
• 化学式: C₁₃H₉N₅O₆
• 分子量: 331.244
• InChiKey: CGAQCEXXWFSNEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  156
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,2,2-三氯-1-(1-甲基-1H-吡咯-2-基)-乙酮 在 硝酸 、 一水合肼 、 三氯氧磷 作用下， 以 乙醇 、 乙酸酐 为溶剂， 反应 5.0h， 生成 2-(2-hydroxy-3-nitrophenyl)-5-(1-methyl-4-nitro-1H-pyrrol-2-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis and evaluation of novel 4-nitropyrrole-based 1,3,4-oxadiazole derivatives as antimicrobial and anti-tubercular agents

  摘要：

  We report synthesis and antimicrobial evaluation of 42 novel 4-nitropyrrole-based 1,3,4-oxadiazoles. The synthesized molecules were evaluated for anti-bacterial, anti-fungal and anti-tubercular activities. Promisingly, most of the compounds showed equal or more potency than standard ciprofloxacin against Staphylococcus aureus, Bacillus subtilis and Escherichia coll. Compound 5e exhibited highest antitubercular activity (0.46 mu g/mL) close to that of standard Isoniazid (0.40 mu g/mL). Equal antifungal activity (1.56 mu g/mL) compared to standard Amphotericin-B was shown by most of the compounds. All the N-methylated compounds showed more potent to equal activity against MSSA (MIC 0.39-1.56 mu g/mL) and MRSA (MIC 0.78-1.56 mu g/mL). All compounds were tested for mammalian cell toxicity using VERO cell line and were found to be non-toxic. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.09.039

文献信息

• Synthesis and evaluation of novel 4-nitropyrrole-based 1,3,4-oxadiazole derivatives as antimicrobial and anti-tubercular agents
  作者：Rajesh A. Rane、Pavankumar Bangalore、Sheetal D. Borhade、Preeti K. Khandare

  DOI：10.1016/j.ejmech.2013.09.039

  日期：2013.12

  We report synthesis and antimicrobial evaluation of 42 novel 4-nitropyrrole-based 1,3,4-oxadiazoles. The synthesized molecules were evaluated for anti-bacterial, anti-fungal and anti-tubercular activities. Promisingly, most of the compounds showed equal or more potency than standard ciprofloxacin against Staphylococcus aureus, Bacillus subtilis and Escherichia coll. Compound 5e exhibited highest antitubercular activity (0.46 mu g/mL) close to that of standard Isoniazid (0.40 mu g/mL). Equal antifungal activity (1.56 mu g/mL) compared to standard Amphotericin-B was shown by most of the compounds. All the N-methylated compounds showed more potent to equal activity against MSSA (MIC 0.39-1.56 mu g/mL) and MRSA (MIC 0.78-1.56 mu g/mL). All compounds were tested for mammalian cell toxicity using VERO cell line and were found to be non-toxic. (C) 2013 Elsevier Masson SAS. All rights reserved.