2-(4-nitro-1H-pyrrole-2-carbonyl)-N-(o-tolyl)hydrazinecarbothioamide | 1616261-07-4

• 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
• 英文名称: 2-(4-nitro-1H-pyrrole-2-carbonyl)-N-(o-tolyl)hydrazinecarbothioamide
• 英文别名: 1-(2-methylphenyl)-3-[(4-nitro-1H-pyrrole-2-carbonyl)amino]thiourea
• CAS: 1616261-07-4
• 化学式: C₁₃H₁₃N₅O₃S
• 分子量: 319.344
• InChiKey: UXHQTMYQXUZKHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  147
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 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 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-(4-nitro-1H-pyrrole-2-carbonyl)-N-(o-tolyl)hydrazinecarbothioamide
  参考文献：
  名称：

  Synthesis of novel 4-nitropyrrole-based semicarbazide and thiosemicarbazide hybrids with antimicrobial and anti-tubercular activity

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2014.05.018