Ethyl 2-(4-chlorophenyl)-1-(2-hydroxyethyl)benzimidazole-5-carboxylate | 1542559-41-0

• 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-chlorophenyl)-1-(2-hydroxyethyl)benzimidazole-5-carboxylate
• 英文别名: ethyl 2-(4-chlorophenyl)-1-(2-hydroxyethyl)benzimidazole-5-carboxylate
• CAS: 1542559-41-0
• 化学式: C₁₈H₁₇ClN₂O₃
• 分子量: 344.798
• InChiKey: QKFDTAGQRRRQMX-UHFFFAOYSA-N

物化性质

• 沸点：
  537.0±60.0 °C(predicted)
• 密度：
  1.31±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 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：
  64.4
• 氢给体数：
  1
• 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 10% palladium 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-chlorophenyl)-1-(2-hydroxyethyl)benzimidazole-5-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of novel benzimidazole derivatives as sirtuin inhibitors with antitumor activities

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2013.12.029

文献信息

• 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.