N-p-nitrobenzyl-o-phenylenediamine | 7288-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-p-nitrobenzyl-o-phenylenediamine
• 英文别名: N-(4-Nitrobenzyl)-o-phenylendiamin；N-(4-Nitrobenzyl)benzene-1,2-diamine；2-N-[(4-nitrophenyl)methyl]benzene-1,2-diamine
• CAS: 7288-53-1
• 化学式: C₁₃H₁₃N₃O₂
• 分子量: 243.265
• InChiKey: BULXRVNHQUYFRY-UHFFFAOYSA-N

物化性质

• 熔点：
  136-139 °C
• 沸点：
  451.5±30.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  83.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-p-nitrobenzyl-o-phenylenediamine 在 盐酸 、 potassium carbonate 、 potassium iodide 作用下， 以 水 、 乙腈 为溶剂， 反应 4.0h， 生成 1-cyclopropyl-6-fluoro-7-(4-((1-(4-nitrobenzyl)-1H-benzimidazol-2-yl)methyl)piperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  Discovery of membrane active benzimidazole quinolones-based topoisomerase inhibitors as potential DNA-binding antimicrobial agents

  摘要：

  A series of novel benzimidazole quinolones as potential antimicrobial agents were designed and synthesized. Most of the prepared compounds exhibited good or even stronger antimicrobial activities in comparison with reference drugs. The most potent compound 15m was membrane active and did not trigger the development of resistance in bacteria. It not only inhibited the formation of biofilms but also disrupted the established Staphylococcus aureus and Escherichia coli biofilms. It was able to inhibit the relaxation activity of E. coli topoisomerase IV at 10 mu M concentration. Moreover, this compound also showed low toxicity against mammalian cells. Molecular modeling and experimental investigation of compound 15m with DNA suggested that this compound could effectively bind with DNA to form a steady 15m-DNA complex which might further block DNA replication to exert the powerful bioactivities. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.01.052
• 作为产物：
  描述：

  4-硝基苄胺 在 potassium carbonate 、 氯化铵 、 锌 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 N-p-nitrobenzyl-o-phenylenediamine
  参考文献：
  名称：

  CuBr-Catalyzed Oxidation/Coupling: An Efficient and Applicable Strategy for the Synthesis of 2-Aryl Benzimidazoles from 1-Fluoro-2-nitrobenzene and Benzylamines

  摘要：

  A novel and efficient route has been developed for the synthesis of benzimidazole derivatives via ligand-free CuBr-catalyzed oxidation and cyclization of 1,2-diamines derived from 1-fluoro-2-nitrobenzene and different arylamines as starting materials.

  DOI：

  10.1080/00397911.2014.971971

文献信息

• Synthesis of novel calix[4]arene <i>p</i>-benzazole derivatives and investigation of their DNA binding and cleavage activities with molecular docking and experimental studies
  作者：Seyda Cigdem Ozkan、Fatma Aksakal、Aydan Yilmaz

  DOI：10.1039/d0ra07486a

  日期：——

  In this study, novel p-benzimidazole-derived calix[4]arene compounds with different structures, and a benzothiazole-derived calix[4]arene compound, were synthesized by a microwave-assisted method and their structures were determined by FTIR, 1H NMR, 13C NMR, MALDI-TOF mass spectroscopy, and elemental analysis. The effects of functional calixarenes against bacterial (pBR322 plasmid DNA) and eukaryotic

  本研究通过微波辅助方法合成了不同结构的新型对苯并咪唑衍生的杯[4]芳烃化合物以及苯并噻唑衍生的杯[4]芳烃化合物，并通过FTIR、1 H确定了它们的结构。 NMR、13 C NMR、MALDI-TOF 质谱和元素分析。研究了功能性杯芳烃对细菌（pBR322 质粒 DNA）和真核 DNA（小牛胸腺 DNA = CT-DNA）的影响。对质粒DNA的研究表明，分别含有甲基和苄基的化合物6和10在最高浓度（10 000 μM）下具有DNA切割活性。还研究了使用一些限制性酶（ BamHI和HindIII ）与质粒 DNA 的相互作用。使用紫外-可见光谱和荧光光谱检查对位取代的杯[4]芳烃化合物对CT-DNA的结合能力，并确定一些化合物显示出效率。特别是，观察到含有苄基和氯基团的功能化合物（ 10和5 ）具有更高的活性（发现K b结合常数分别为 7.1 × 10 3 M -1和 9.3 × 10 2 M
• Synthesis, structure and reactivity of 1-(4-nitrobenzyl)-2-chloromethyl benzimidazole
  作者：Amanda E. Sparke、Christopher M. Fisher、Ryan E. Mewis、Stephen J. Archibald

  DOI：10.1016/j.tetlet.2010.07.010

  日期：2010.9

  synthesis of 1-(4-nitrobenzyl)-2-chloromethyl benzimidazole, which undergoes a nucleophilic substitution with pyridine in the absence of additional base, is reported. The key steps are the reaction of 1,2-phenylenediamine to give exclusively the mono-substituted product and the avoidance of minor by-products via the use of glycolic acid for the cyclisation step. The X-ray structures of 1-(4-nitrobenzyl)-2-chloromethyl

  据报道1-（4-硝基苄基）-2-氯甲基苯并咪唑的合成，其在不存在另外的碱的情况下被吡啶亲核取代。关键步骤是1,2-苯二胺的反应，仅得到单取代的产物，通过在环化步骤中使用乙醇酸避免副产物的产生。给出了1-（4-硝基苄基）-2-氯甲基苯并咪唑氯化物和1- [1-（4-硝基苄基）苯并咪唑-2-基甲基]吡啶鎓氯化物的X射线结构。
• Metal-Free TEMPO-Promoted C(sp³)–H Amination To Afford Multisubstituted Benzimidazoles
  作者：Ding Xue、Ya-Qiu Long

  DOI：10.1021/jo5005179

  日期：2014.5.16

  An efficient TEMPO-air/cat. TEMPO-O-2 oxidative protocol was developed to synthesize multisubstituted or fused tetracyclic benzimidazoles via a metal-free oxidative C-N coupling between the sp(3) C-H and free N-H of readily available N-1-benzyl/alkyl-1,2-phenylenediamines.
• Multifunctional PdAg@MIL-101 for One-Pot Cascade Reactions: Combination of Host–Guest Cooperation and Bimetallic Synergy in Catalysis
  作者：Yu-Zhen Chen、Yu-Xiao Zhou、Hengwei Wang、Junling Lu、Takeyuki Uchida、Qiang Xu、Shu-Hong Yu、Hai-Long Jiang

  DOI：10.1021/cs501953d

  日期：2015.4.3

  Metal nanoparticles (NPs) stabilized by metal-organic frameworks (MOFs) are very promising for catalysis, while reports on their cooperative catalysis for a cascade reaction have been very rare. In this work, Pd NPs incorporated into a MOF, MIL-101, have jointly completed a tandem reaction on the basis of MOF Lewis acidity and Pd NPs. Subsequently, ultrafine PdAg alloy NPs (similar to 1.5 nm) have been encapsulated into MIL-101. The obtained multifunctional PdAg@MIL-101 exhibits good catalytic activity and selectivity in cascade reactions under mild conditions, on the basis of the combination of host-guest cooperation and bimetallic synergy, where MIL-101 affords Lewis acidity and Pd offers hydrogenation activity while Ag greatly improves selectivity to the target product. As far as we know, this is the first work on bimetallic NP@MOFs as multifunctional catalysts with multiple active sites (MOF acidity and bimetallic species) that exert respective functions and cooperatively catalyze a one-pot cascade reaction.