ethyl 2-(4-nitrophenyl)-1-(3-(2-oxopyrrolidin-1-yl)propyl)-1H-benzo[d]imidazole-5-carboxylate | 1377136-59-8

• 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-nitrophenyl)-1-(3-(2-oxopyrrolidin-1-yl)propyl)-1H-benzo[d]imidazole-5-carboxylate
• 英文别名: Ethyl 2-(4-nitrophenyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]-1H-benzimidazole-5-carboxylate；ethyl 2-(4-nitrophenyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]benzimidazole-5-carboxylate
• CAS: 1377136-59-8
• 化学式: C₂₃H₂₄N₄O₅
• 分子量: 436.467
• InChiKey: ZKVPZCNVOWNZMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

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， 反应 3.0h， 生成 ethyl 2-(4-nitrophenyl)-1-(3-(2-oxopyrrolidin-1-yl)propyl)-1H-benzo[d]imidazole-5-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of antimycobacterial activity of new benzimidazole aminoesters

  摘要：

  A total of 51 novel benzimidazoles were synthesized by a 4-step reaction starting from basic compound 4-fluoro-3-nitrobenzoic acid under relatively mild reaction conditions. The structure of the novel benzimidazoles was confirmed by mass spectra as well as H-1 NMR spectroscopic data. Out of the 51 novel synthesized compounds, 42 of them were screened for their antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv strain using BacTiter-Glo (TM) Microbial Cell Viability (BTG) method. Results of activity screened using Alamar Blue method was also provided for comparison purposes. Two of the novel benzimidazoles synthesized showed moderately good activity with 1050 of less than 15 mu M. Compound 5g, ethyl 2-(4-(trifluoromethyl)phenyl)-1-(2-morpholinoethyl)-1H-benzo[d]imidazole-5-carboxylate, was found to be the most active with IC50 of 11.52 mu M. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.025

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.
• Synthesis and evaluation of antimycobacterial activity of new benzimidazole aminoesters
  作者：Yeong Keng Yoon、Mohamed Ashraf Ali、Ang Chee Wei、Tan Soo Choon、Rusli Ismail

  DOI：10.1016/j.ejmech.2013.06.025

  日期：2015.3

  A total of 51 novel benzimidazoles were synthesized by a 4-step reaction starting from basic compound 4-fluoro-3-nitrobenzoic acid under relatively mild reaction conditions. The structure of the novel benzimidazoles was confirmed by mass spectra as well as H-1 NMR spectroscopic data. Out of the 51 novel synthesized compounds, 42 of them were screened for their antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv strain using BacTiter-Glo (TM) Microbial Cell Viability (BTG) method. Results of activity screened using Alamar Blue method was also provided for comparison purposes. Two of the novel benzimidazoles synthesized showed moderately good activity with 1050 of less than 15 mu M. Compound 5g, ethyl 2-(4-(trifluoromethyl)phenyl)-1-(2-morpholinoethyl)-1H-benzo[d]imidazole-5-carboxylate, was found to be the most active with IC50 of 11.52 mu M. (C) 2014 Elsevier Masson SAS. All rights reserved.