N-((1H-benzo[d]imidazol-2-yl)methyl)-2,4-dichloroaniline | 73259-52-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N-((1H-benzo[d]imidazol-2-yl)methyl)-2,4-dichloroaniline
• 英文别名: N-(1H-benzoimidazol-2-ylmethyl)-2,4-dichloro-aniline；N-(1H-benzimidazol-2-ylmethyl)-2,4-dichloroaniline
• CAS: 73259-52-6
• 化学式: C₁₄H₁₁Cl₂N₃
• 分子量: 292.167
• InChiKey: PODNPDRZVMMJIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  40.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-二氟溴苄 、 N-((1H-benzo[d]imidazol-2-yl)methyl)-2,4-dichloroaniline 在 potassium carbonate 作用下， 以 乙腈 、 水 为溶剂， 反应 48.5h， 以34%的产率得到1,3-bis(2,4-difluorobenzyl)-1H-benzo[d]imidazol-2(3H)-one
  参考文献：
  名称：

  A unique one-pot reaction via CC cleavage from aminomethylene benzimidazoles to access benzimidazolones with wide potentiality

  摘要：

  A unique one-pot reaction via C-C cleavage from aminomethylene benzimidazoles with commercial halides to access novel benzimidazolones is reported for the first time. The previously unexploited transformation is able to perform smoothly in the presence of commercial potassium carbonate, while the stronger inorganic bases or organic amines as catalysts are not favorable to the transformation. Significant influential factors including base, temperature, solvent, water content, and molar ratio of substrates to this reaction are investigated, and possibly mechanistic consideration is also discussed. Some synthesized benzimidazolones were evaluated and exhibited better bioactivities against tested strains than clinical drugs chloromycin, norfloxacin, and fluconazole. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.05.113
• 作为产物：
  描述：

  邻苯二胺 在 盐酸 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 生成 N-((1H-benzo[d]imidazol-2-yl)methyl)-2,4-dichloroaniline
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel benzimidazole derivatives and their interaction with calf thymus DNA and synergistic effects with clinical drugs

  摘要：

  一系列新的苯并咪唑衍生物被合成并通过红外（IR）、氢核磁共振（1H NMR）、碳核磁共振（13C NMR）、质谱（MS）和高效液相色谱（HRMS）谱图进行了表征。所有新化合物通过两倍系列稀释技术在体外进行了抗微生物活性筛选。生物活性评估显示，3,5-双(三氟甲基)苯基苯并咪唑的抗菌和抗真菌活性与参考药物氯霉素、诺氟沙星和氟康唑相当或更强。2,4-二氟苄基苯并咪唑衍生物5l及其盐酸盐7分别与抗菌药物氯霉素、诺氟沙星和抗真菌药物氟康唑的联合使用，对耐甲氧西林的金黄色葡萄球菌（MRSA）和氟康唑不敏感的黄曲霉菌（A. flavus）更为敏感。此外，化合物5l与小牛胸腺DNA的相互作用表明，该化合物能有效嵌入DNA中形成化合物5l-DNA复合物，可能阻断DNA复制，从而发挥良好的抗微生物活性。

  DOI：

  10.1007/s11426-014-5087-x

文献信息

• Design, synthesis and antimicrobial evaluation of novel benzimidazole type of Fluconazole analogues and their synergistic effects with Chloromycin, Norfloxacin and Fluconazole
  作者：Hui-Zhen Zhang、Guri L.V. Damu、Gui-Xin Cai、Cheng-He Zhou

  DOI：10.1016/j.ejmech.2013.03.049

  日期：2013.6

  A novel series of benzimidazole type of Fluconazole analogues were synthesized and characterized by H-1 NMR, C-13 NMR, IR, MS and HRMS spectra. All the new compounds were screened for their antimicrobial activities in vitro by two-fold serial dilution technique. The bioactive evaluation showed that 3,5-bis(trifluoromethyl)phenyl benzimidazoles gave comparable or even stronger antibacterial and antifungal efficiency in comparison with reference drugs Chloromycin, Norfloxacin and Fluconazole. The combination of 2,4-difluorobenzyl benzimidazole derivative 5m and its hydrochloride 7 respectively with antibacterial Chloromycin, Norfloxacin or antifungal Fluconazole showed better antimicrobial efficiency with less dosage and broader antimicrobial spectrum than the separated use of them alone. Notably, these combined systems were more sensitive to Fluconazole-insensitive Aspergillus flavus and methicillin-resistant MRSA. (C) 2013 Elsevier Masson SAS. All rights reserved.
• A unique one-pot reaction via CC cleavage from aminomethylene benzimidazoles to access benzimidazolones with wide potentiality
  作者：Hui-Zhen Zhang、Sheng-Feng Cui、Sangaraiah Nagarajan、Syed Rasheed、Gui-Xin Cai、Cheng-He Zhou

  DOI：10.1016/j.tetlet.2014.05.113

  日期：2014.7

  A unique one-pot reaction via C-C cleavage from aminomethylene benzimidazoles with commercial halides to access novel benzimidazolones is reported for the first time. The previously unexploited transformation is able to perform smoothly in the presence of commercial potassium carbonate, while the stronger inorganic bases or organic amines as catalysts are not favorable to the transformation. Significant influential factors including base, temperature, solvent, water content, and molar ratio of substrates to this reaction are investigated, and possibly mechanistic consideration is also discussed. Some synthesized benzimidazolones were evaluated and exhibited better bioactivities against tested strains than clinical drugs chloromycin, norfloxacin, and fluconazole. (C) 2014 Elsevier Ltd. All rights reserved.
• Design, synthesis, and biological evaluation of novel benzimidazole derivatives and their interaction with calf thymus DNA and synergistic effects with clinical drugs
  作者：HuiZhen Zhang、JianMei Lin、Syed Rasheed、ChengHe Zhou

  DOI：10.1007/s11426-014-5087-x

  日期：2014.6

  A series of new benzimidazole derivatives was synthesized and characterized by IR, 1H NMR, 13C NMR, MS, and HRMS spectra. All the new compounds were screened for their antimicrobial activities in vitro by a twofold serial dilution technique. The bioactive evaluation showed that 3,5-bis(trifluoromethyl)phenyl benzimidazoles were comparably or even more strongly antibacterial and antifungal than the reference drugs Chloromycin, Norfloxacin, and Fluconazole. The combination of 2,4-difluorobenzyl benzimidazole derivative 5l and its hydrochloride 7 respectively with the antibacterials Chloromycin, Norfloxacin, and the antifungal Fluconazole was more sensitive to methicillin-resistant MRSA and Fluconazole-insensitive A. flavus. In addition, the interaction of compound 5l with calf thymus DNA demonstrated that this compound could effectively intercalate into DNA to form a compound 5l-DNA complex that might block DNA replication and thereby exert good antimicrobial activity.

  一系列新的苯并咪唑衍生物被合成并通过红外（IR）、氢核磁共振（1H NMR）、碳核磁共振（13C NMR）、质谱（MS）和高效液相色谱（HRMS）谱图进行了表征。所有新化合物通过两倍系列稀释技术在体外进行了抗微生物活性筛选。生物活性评估显示，3,5-双(三氟甲基)苯基苯并咪唑的抗菌和抗真菌活性与参考药物氯霉素、诺氟沙星和氟康唑相当或更强。2,4-二氟苄基苯并咪唑衍生物5l及其盐酸盐7分别与抗菌药物氯霉素、诺氟沙星和抗真菌药物氟康唑的联合使用，对耐甲氧西林的金黄色葡萄球菌（MRSA）和氟康唑不敏感的黄曲霉菌（A. flavus）更为敏感。此外，化合物5l与小牛胸腺DNA的相互作用表明，该化合物能有效嵌入DNA中形成化合物5l-DNA复合物，可能阻断DNA复制，从而发挥良好的抗微生物活性。