ethyl 1-(3-(2-oxopyrrolidin-1-yl)propyl)-2-p-tolyl-1H-benzo[d]imidazole-5-carboxylate | 1620558-15-7

• 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-(2-oxopyrrolidin-1-yl)propyl)-2-p-tolyl-1H-benzo[d]imidazole-5-carboxylate
• 英文别名: Ethyl 2-(4-methylphenyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]benzimidazole-5-carboxylate；ethyl 2-(4-methylphenyl)-1-[3-(2-oxopyrrolidin-1-yl)propyl]benzimidazole-5-carboxylate
• CAS: 1620558-15-7
• 化学式: C₂₄H₂₇N₃O₃
• 分子量: 405.497
• InChiKey: YSXNVYMJKJWSKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.4
• 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 sodium meta bi sulfate 、 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 ethyl 1-(3-(2-oxopyrrolidin-1-yl)propyl)-2-p-tolyl-1H-benzo[d]imidazole-5-carboxylate
  参考文献：
  名称：

  Benzimidazoles as new scaffold of sirtuin inhibitors: Green synthesis, in vitro studies, molecular docking analysis and evaluation of their anti-cancer properties

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2014.06.060

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.