4-硝基-1H-吡咯-2-苯甲醛 | 28494-48-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 4-硝基-1H-吡咯-2-苯甲醛
• 英文名称: 4-nitro-1H-pyrrole-2-carbohydrazide
• 英文别名: 4-Nitropyrrol-2-carbonsaeurehydrazid
• CAS: 28494-48-6
• 化学式: C₅H₆N₄O₃
• mdl: MFCD07339177
• 分子量: 170.128
• InChiKey: ZBSOAZSDZAQXCU-UHFFFAOYSA-N

物化性质

• 熔点：
  286-288°

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  117
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  4-硝基-1H-吡咯-2-苯甲醛 、 2-溴苯甲酸 在 三氯氧磷 作用下， 以87%的产率得到2-(2-bromophenyl)-5-(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
• 作为产物：
  描述：

  2,2,2-三氯-1-(4-硝基-1H-吡咯-2-基)-乙酮 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以69%的产率得到4-硝基-1H-吡咯-2-苯甲醛
  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 of novel 4-nitropyrrole-based semicarbazide and thiosemicarbazide hybrids with antimicrobial and anti-tubercular activity
  作者：Rajesh A. Rane、Shital S. Naphade、Pavan Kumar Bangalore、Mahesh B. Palkar、Mahamadhanif S. Shaikh、Rajshekhar Karpoormath

  DOI：10.1016/j.bmcl.2014.05.018

  日期：2014.7

  We report the synthesis and screening of forty novel 4-nitropyrrole-semicarbazide conjugates inspired from the reported bio-potential of bromopyrrole alkaloids and semicarbazide derivatives for antimicrobial activity. Herein, hybrids 5k-5o, 5r, 5s and 5t displayed four-fold increased activity (MIC = 0.39 mu g/mL) against Escherichia coli compared to standard ciprofloxacin. Eight hybrids, 5k-5o and 5r-5t displayed equal antibacterial activity (MIC = 1.56 mu g/mL) against Klebsiella pneumonia compared to standard ciprofloxacin. Hybrid, 5k-5o (MIC = 0.195 mu g/mL) displayed highly potent antibacterial activity against MSSA as compared to standard ciprofloxacin. Eight-fold superior activity was observed for four hybrids 5k-5m and 5o (MIC = 0.391 mu g/mL) against MRSA. Further, nine hybrids displayed four-fold superior antifungal activity (MIC = 0.78 mu g/mL) compared to standard Amphotericin B. Encouraging MICs of these hybrids recognize them as promising leads for development of potential antimicrobial drugs. (C) 2014 Elsevier Ltd. All rights reserved.
• 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.