ethyl 1-(2-hydroxyethyl)-2-(4-nitrophenyl)-1H-benzo[d]imidazole-5-carboxylate | 1542559-55-6

• 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: ethyl 1-(2-hydroxyethyl)-2-(4-nitrophenyl)-1H-benzo[d]imidazole-5-carboxylate
• 英文别名: Ethyl 1-(2-hydroxyethyl)-2-(4-nitrophenyl)benzimidazole-5-carboxylate；ethyl 1-(2-hydroxyethyl)-2-(4-nitrophenyl)benzimidazole-5-carboxylate
• CAS: 1542559-55-6
• 化学式: C₁₈H₁₇N₃O₅
• 分子量: 355.35
• InChiKey: JDHHNMIWQLZHOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  110
• 氢给体数：
  1
• 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 sodium hydrogen sulfate 、 甲酸铵 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 ethyl 1-(2-hydroxyethyl)-2-(4-nitrophenyl)-1H-benzo[d]imidazole-5-carboxylate
  参考文献：
  名称：

  Total Synthesis of Diversified 1,2-disubstituted Benzimidazoles with Green Approach at Room Temperature

  摘要：

  一种绿色、简单的方法已被开发用于合成多样化的1,2-双取代苯并咪唑。整个合成过程在室温下进行，使用水和乙醇作为溶剂。由于水相和乙醇的低毒性和易于回收，该方法非常适合大规模生产。此外，所获得的产品产率高且易于分离，使该方法非常实用和具有吸引力。

  DOI：

  10.2174/157017861110141117150010

文献信息

• Total Synthesis of Diversified 1,2-disubstituted Benzimidazoles with Green Approach at Room Temperature
  作者：Yeong Yoon、Mohamed Ali、Ang Wei、Tan Choon、Lim Leng、Oo Wei

  DOI：10.2174/157017861110141117150010

  日期：2014.11.17

  A green and facile method to synthesize diversified 1,2-disubstituted benzimidazoles has been developed. The total synthesis was performed at room temperature utilizing water and ethanol as solvents. As aqueous media and ethanol have low toxicity and are easily recyclable, the method presented is very suitable for scale-up production. Furthermore, products were obtained in high yield and easily isolated making this method very practical and attractive.

  一种绿色、简单的方法已被开发用于合成多样化的1,2-双取代苯并咪唑。整个合成过程在室温下进行，使用水和乙醇作为溶剂。由于水相和乙醇的低毒性和易于回收，该方法非常适合大规模生产。此外，所获得的产品产率高且易于分离，使该方法非常实用和具有吸引力。
• Synthesis and evaluation of novel benzimidazole derivatives as sirtuin inhibitors with antitumor activities
  作者：Yeong Keng Yoon、Mohamed Ashraf Ali、Ang Chee Wei、Tan Soo Choon、Hasnah Osman、Keykavous Parang、Amir Nasrolahi Shirazi

  DOI：10.1016/j.bmc.2013.12.029

  日期：2014.1

  A total of 15 novel benzimidazole derivatives were designed, synthesized and evaluated for their SIRT1 and SIRT2 inhibitory activity. All compounds showed better inhibition on SIRT2 as compared to SIRT1. Among these, compound 5j displayed the best inhibitory activity for SIRT1 (IC50 = 58.43 mu M) as well as for SIRT2 (IC50 = 45.12 mu M). Cell cytotoxicity assays also showed that compound 5j possesses good antitumor activity against two different cancer cell lines derived frombreast cancer (MCF-7 and MDA-MB-468). A simple structure-activity-relationship (SAR) study of the newly synthesized benzimidazole derivatives was also discussed. (C) 2013 Elsevier Ltd. All rights reserved.