ethyl 2-(4-nitrophenyl)-1-phenyl-1H-benzo[d]imidazole-5-carboxylate | 1620558-21-5

• 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-nitrophenyl)-1-phenyl-1H-benzo[d]imidazole-5-carboxylate
• 英文别名: Ethyl 2-(4-nitrophenyl)-1-phenylbenzimidazole-5-carboxylate；ethyl 2-(4-nitrophenyl)-1-phenylbenzimidazole-5-carboxylate
• CAS: 1620558-21-5
• 化学式: C₂₂H₁₇N₃O₄
• 分子量: 387.395
• InChiKey: LWECYQHFOBASBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 3-nitro-4-(phenylamino)benzoate 在 sodium metabisulfite 、 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 ethyl 2-(4-nitrophenyl)-1-phenyl-1H-benzo[d]imidazole-5-carboxylate
  参考文献：
  名称：

  通过多步合成对苯并咪唑进行结构修饰及其对 Sirtuin 抑制活性的影响

  摘要：

  苯并咪唑衍生物已被证明具有抑制沉默调节蛋白的活性。在不断寻找有效的sirtuin抑制剂的过程中，对先前鉴定的苯并咪唑类sirtuin抑制剂末端苯环进行了系统的改变，以进一步研究它们的构效关系。结果表明，这些新化合物的sirtuin活性遵循除卤代取代基外，间位取代化合物的效力明显弱于邻位和对位取代化合物的趋势。进行分子对接研究以使这些观察合理化。除此之外，还讨论了用于合成有趣化合物的方法。

  DOI：

  10.1002/ardp.201500337

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.
• Structural Modifications of Benzimidazoles via Multi-Step Synthesis and Their Impact on Sirtuin-Inhibitory Activity
  作者：Yeong Keng Yoon、Tan Soo Choon

  DOI：10.1002/ardp.201500337

  日期：2016.1

  Benzimidazole derivatives have been shown to possess sirtuin‐inhibitory activity. In the continuous search for potent sirtuin inhibitors, systematic changes on the terminal benzene ring were performed on previously identified benzimidazole‐based sirtuin inhibitors, to further investigate their structure–activity relationships. It was demonstrated that the sirtuin activities of these novel compounds

  苯并咪唑衍生物已被证明具有抑制沉默调节蛋白的活性。在不断寻找有效的sirtuin抑制剂的过程中，对先前鉴定的苯并咪唑类sirtuin抑制剂末端苯环进行了系统的改变，以进一步研究它们的构效关系。结果表明，这些新化合物的sirtuin活性遵循除卤代取代基外，间位取代化合物的效力明显弱于邻位和对位取代化合物的趋势。进行分子对接研究以使这些观察合理化。除此之外，还讨论了用于合成有趣化合物的方法。