2-methyl-4(5)-nitro-5(4)-(1-piperidyl)imidazole | 139520-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-4(5)-nitro-5(4)-(1-piperidyl)imidazole
• 英文别名: 1-(2-methyl-5-nitro-1H-imidazol-4-yl)piperidine
• CAS: 139520-07-3
• 化学式: C₉H₁₄N₄O₂
• 分子量: 210.236
• InChiKey: HUSPGTDUHXTAEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  77.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-6-fluoro-7-(4-(oxiran-2-ylmethyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 、 2-methyl-4(5)-nitro-5(4)-(1-piperidyl)imidazole 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 21.0h， 以25.3%的产率得到cyclopropyl-6-fluoro-7-(4-(2-hydroxy-3-(2-methyl-5-nitro-4-(piperidin-1-yl)-1H-imidazol-1-yl)propyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Design and biological evaluation of novel quinolone-based metronidazole derivatives as potent Cu2+ mediated DNA-targeting antibacterial agents

  摘要：

  A series of novel quinolone-based metronidazole derivatives as new type of antimicrobial agents were developed and characterized. Most of them gave good antibacterial activity towards the Gram-positive and negative bacteria. Noticeably, quinolone derivative 3i exhibited low MIC value of 0.25 mu g/mL against Pseudomonas aeruginosa, which was even superior to reference drugs Norfloxacin, Ciprofloxacin and Clinafloxacin. The further research revealed that compound 3i could intercalate into P. aeruginosa DNA through copper ion bridge to form a steady 3i-Cu2+-DNA ternary complex which might further block DNA replication to exert the powerful bioactivities. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.06.041
• 作为产物：
  描述：

  1-[3-(2-Ethanesulfonyl-ethyl)-2-methyl-5-nitro-3H-imidazol-4-yl]-piperidine 在 sodium isopropylate 作用下， 以 异丙醇 为溶剂， 反应 0.33h， 以81%的产率得到2-methyl-4(5)-nitro-5(4)-(1-piperidyl)imidazole
  参考文献：
  名称：

  Novel Synthesis of 4(5)-Cyclic Amino-5(4)-nitroimidazoles

  摘要：

  A novel two step sequence for the synthesis of hitherto inaccessible 4(5)-cyclic amino-5(4)-nitroimidazoles is described.

  DOI：

  10.1080/00397919408011193

文献信息

• Salwinska, Ewa; Suwinski, Jerzy; Bialecki, Maciej, Polish Journal of Chemistry, 1991, vol. 65, # 5-6, p. 1071 - 1075
  作者：Salwinska, Ewa、Suwinski, Jerzy、Bialecki, Maciej

  DOI：——

  日期：——
• Design and biological evaluation of novel quinolone-based metronidazole derivatives as potent Cu2+ mediated DNA-targeting antibacterial agents
  作者：Ling Zhang、Kannekanti Vijaya Kumar、Rong-Xia Geng、Cheng-He Zhou

  DOI：10.1016/j.bmcl.2015.06.041

  日期：2015.9

  A series of novel quinolone-based metronidazole derivatives as new type of antimicrobial agents were developed and characterized. Most of them gave good antibacterial activity towards the Gram-positive and negative bacteria. Noticeably, quinolone derivative 3i exhibited low MIC value of 0.25 mu g/mL against Pseudomonas aeruginosa, which was even superior to reference drugs Norfloxacin, Ciprofloxacin and Clinafloxacin. The further research revealed that compound 3i could intercalate into P. aeruginosa DNA through copper ion bridge to form a steady 3i-Cu2+-DNA ternary complex which might further block DNA replication to exert the powerful bioactivities. (C) 2015 Elsevier Ltd. All rights reserved.
• Novel Synthesis of 4(5)-Cyclic Amino-5(4)-nitroimidazoles
  作者：Rao、Rao、Singh

  DOI：10.1080/00397919408011193

  日期：1994.2

  A novel two step sequence for the synthesis of hitherto inaccessible 4(5)-cyclic amino-5(4)-nitroimidazoles is described.