8-(4-nitro-phenyl)-7H-acenaphtho[1,2-d]imidazole | 17988-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 8-(4-nitro-phenyl)-7H-acenaphtho[1,2-d]imidazole
• 英文别名: 8-(4-nitro-phenyl)-7H-acenaphth[1,2-d]imidazole；8-(4-Nitro-phenyl)-7H-acenaphth[1,2-d]imidazol；8-(4-Nitrophenyl)-7H-acenaphtho[1,2-d]imidazole；8-(4-nitrophenyl)-7H-acenaphthyleno[1,2-d]imidazole
• CAS: 17988-08-8
• 化学式: C₁₉H₁₁N₃O₂
• 分子量: 313.315
• InChiKey: HXMJYUDWPACKJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-(4-nitro-phenyl)-7H-acenaphtho[1,2-d]imidazole 在 palladium on activated charcoal 、 肼 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  A highly substituted and fluorescent aromatic-fused imidazole derivative that shows enhanced antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA)

  摘要：

  A novel highly substituted and fluorescent aromatic-fused imidazole derivative has been synthesized by rational design. This novel fluorescent material acts as an alternative antibacterial agent against Gram positive bacteria strains. It shows superior antibacterial activity (with MIC value of 8 mu g/mL) against methicillin-resistant Staphylococcus aureus (MRSA) when compared with standard antibiotic drugs Ampicillin (with MIC value of 128 mu g/mL) and Kanamycin (with MIC value of > 512 mu g/mL). The interaction of this novel compound with the bacterial cell and genomic DNA has also been studied to elucidate antibacterial mode of action. Fluorescence spectroscopy and microscopy studies have proved the intracellular uptake of this special compound. Likewise, UV-vis and fluorescence spectroscopy studies have revealed a significant decrease in the absorption and emission bands of the compound upon its interaction with plasmid and genomic DNA, which is likely due to its DNA intercalation property. Furthermore, these findings have been supported by gel electrophoresis of genomic DNA of S. aureus cells treated with the compound. The results indicate that this novel compound exerts its antibacterial activity by causing DNA damage, suggesting the potential utility of fluorescent probes for real-time diagnosis and treatment of bacterial infections.

  DOI：

  10.1016/j.jhazmat.2020.122902
• 作为产物：
  描述：

  对硝基苯甲醛 、 苊醌 在 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.5h， 以95%的产率得到8-(4-nitro-phenyl)-7H-acenaphtho[1,2-d]imidazole
  参考文献：
  名称：

  氧化石墨烯官能化硫酸二乙醇胺作为一种新型、高效、可持续的催化剂，用于合成 8-aryl-7H-苊并[1,2-d]咪唑

  摘要：

  8-Aryl-7 H-苊[1,2- d] 咪唑是通过利用硫酸二乙醇胺官能化氧化石墨烯的催化工艺生产的。该过程使用苊醌、乙酸铵和芳香醛在无溶剂条件下通过一锅法反应实施。所应用的催化剂以高产率平稳地催化反应。开发的催化剂具有多种优势，包括碳结构、生态友好性、成本效益以及易于处理和储存。所应用的程序还表现出优于报道的程序的几个优先事项，例如高产率、短反应时间、无副产物、环境相容性和简单的后处理。还在五个循环中检查了催化剂的耐久性和稳定性，结果表明催化活性没有显着降低。

  DOI：

  10.1007/s11164-022-04821-7

文献信息

• Sircar; Sen, Journal of the Indian Chemical Society, 1931, vol. 8, p. 612
  作者：Sircar、Sen

  DOI：——

  日期：——