ethyl 2-(4-(trifluoromethyl)phenyl)-1-phenyl-1H-benzo[d]imidazole-5-carboxylate | 1403460-44-5

• 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 2-(4-(trifluoromethyl)phenyl)-1-phenyl-1H-benzo[d]imidazole-5-carboxylate
• 英文别名: Ethyl 2-(4-(trifluoromethyl)phenyl)-1-phenyl-1h-benzo[d]imidazole-5-carboxylate；ethyl 1-phenyl-2-[4-(trifluoromethyl)phenyl]benzimidazole-5-carboxylate
• CAS: 1403460-44-5
• 化学式: C₂₃H₁₇F₃N₂O₂
• 分子量: 410.395
• InChiKey: PVRNLHNPYWVLHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 3-nitro-4-(phenylamino)benzoate 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 ethyl 2-(4-(trifluoromethyl)phenyl)-1-phenyl-1H-benzo[d]imidazole-5-carboxylate
  参考文献：
  名称：

  Antituberculosis agents bearing the 1,2-disubstituted benzimidazole scaffold

  摘要：

  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.

  DOI：

  10.1007/s00044-017-1784-2

文献信息

• Benzimidazoles as new scaffold of sirtuin inhibitors: Green synthesis, in vitro studies, molecular docking analysis and evaluation of their anti-cancer properties
  作者：Yeong Keng Yoon、Mohamed Ashraf Ali、Ang Chee Wei、Amir Nasrolahi Shirazi、Keykavous Parang、Tan Soo Choon

  DOI：10.1016/j.ejmech.2014.06.060

  日期：2014.8

  Two series of novel benzimidazole derivatives were designed, synthesized and evaluated for their SIRT1 and SIRT2 inhibitory activity. Among the newly synthesized compounds, compound 4j displayed the best inhibitory activity for SIRT1 (IC50 = 54.21 μM) as well as for SIRT2 (IC50 = 26.85 μM). Cell proliferation assay showed that compound 4j possessed good antitumor activity against three different types of cancer cells derived from colon (HCT-116), breast (MDA-MB-468) and blood-leukemia (CCRF-CEM) with cell viability of 40.0%, 53.2% and 27.2% respectively at 50 μM. Docking analysis of representative compound 4j into SIRT2 indicated that the interaction with receptor was primarily due to hydrogen bonding and π-π stacking interactions.
• 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.