ethyl 1-(3-(1H-imidazol-1-yl)propyl)-2-(4-chlorophenyl)-1H-benzo[d]imidazole-5-carboxylate

• 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: ethyl 1-(3-(1H-imidazol-1-yl)propyl)-2-(4-chlorophenyl)-1H-benzo[d]imidazole-5-carboxylate
• 英文别名: Ethyl 1-(3-(1h-imidazol-1-yl)propyl)-2-(4-chlorophenyl)-1h-benzo[d]imidazole-5-carboxylate；ethyl 2-(4-chlorophenyl)-1-(3-imidazol-1-ylpropyl)benzimidazole-5-carboxylate
• 化学式: C₂₂H₂₁ClN₄O₂
• 分子量: 408.887
• InChiKey: ACVXNYGTYMAIHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氟-3-硝基苯甲酸乙酯 在 palladium 10% on activated carbon 、 甲酸铵 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 1-(3-(1H-imidazol-1-yl)propyl)-2-(4-chlorophenyl)-1H-benzo[d]imidazole-5-carboxylate
  参考文献：
  名称：

  Synthesis, characterization, and molecular docking analysis of novel benzimidazole derivatives as cholinesterase inhibitors

  摘要：

  Two series of novel acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors containing benzimidazole core structure were synthesized by a four-step reaction pathway starting from 4-fluoro-3-nitrobenzoic acid as the basic compound. The structure of the novel benzimidazoles was characterized and confirmed by the elemental and mass spectral analyses as well as H-1 NMR spectroscopic data. Of the 34 novel synthesized compounds, three benzimidazoles revealed AChE inhibition with IC50 < 10 mu M. The highest inhibitory activity (IC50 = 5.12 mu M for AChE and IC50 = 8.63 mu M for BChE) corresponds to the compound 5IIc (ethyl 1-(3-(1H-imidazol-1-yl)propyl)-2-(4-nitrophenyl)-1H-benzo[d]imidazole-5-carboxylate). The relationship between lipophilicity and the chemical structures as well as their limited structure-activity relationship was discussed. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.06.008

文献信息

• Synthesis, characterization, and molecular docking analysis of novel benzimidazole derivatives as cholinesterase inhibitors
  作者：Yeong Keng Yoon、Mohamed Ashraf Ali、Ang Chee Wei、Tan Soo Choon、Kooi-Yeong Khaw、Vikneswaran Murugaiyah、Hasnah Osman、Vijay H. Masand

  DOI：10.1016/j.bioorg.2013.06.008

  日期：2013.8

  Two series of novel acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitors containing benzimidazole core structure were synthesized by a four-step reaction pathway starting from 4-fluoro-3-nitrobenzoic acid as the basic compound. The structure of the novel benzimidazoles was characterized and confirmed by the elemental and mass spectral analyses as well as H-1 NMR spectroscopic data. Of the 34 novel synthesized compounds, three benzimidazoles revealed AChE inhibition with IC50 < 10 mu M. The highest inhibitory activity (IC50 = 5.12 mu M for AChE and IC50 = 8.63 mu M for BChE) corresponds to the compound 5IIc (ethyl 1-(3-(1H-imidazol-1-yl)propyl)-2-(4-nitrophenyl)-1H-benzo[d]imidazole-5-carboxylate). The relationship between lipophilicity and the chemical structures as well as their limited structure-activity relationship was discussed. (C) 2013 Elsevier Inc. All rights reserved.
• Antituberculosis agents bearing the 1,2-disubstituted benzimidazole scaffold
  作者：Keng Yoon Yeong、Chee Wei Ang、Mohamed Ashraf Ali、Hasnah Osman、Soo Choon Tan

  DOI：10.1007/s00044-017-1784-2

  日期：2017.4

  The emergence of drug-resistant strains in recent years has fueled the epidemic of tuberculosis. This necessitates the development of new chemical scaffolds to curb resistant tuberculosis for effective control of this disease. In this study, we have designed and synthesized two series of benzimidazole derivatives. Their antimycobacterial activities were initially evaluated using Mycobacterium tuberculosis H37RV strains. The most potent analog (6h) was further assessed using various drug-resistant M. tuberculosis strains. This report described the importance of benzimidazoles as new antitmycobacterial agents targeting both the M. tuberculosis H37RV as well as the drug-resistant-tuberculosis strains. The trifluoromethyl group which was essential for antimycobacterial activity was also highlighted.