2-(3-hydroxyphenyl)-1H-benzimidazol-5-ol | 1441800-87-8

• 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: 2-(3-hydroxyphenyl)-1H-benzimidazol-5-ol
• 英文别名: 2-(3-hydroxyphenyl)-3H-benzimidazol-5-ol
• CAS: 1441800-87-8
• 化学式: C₁₃H₁₀N₂O₂
• mdl: MFCD25587355
• 分子量: 226.235
• InChiKey: URMFIKOQSKQRHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(5-methoxy-1H-benzimidazol-2-yl)phenol 在 氢溴酸 、 溶剂黄146 作用下， 反应 24.0h， 以85%的产率得到2-(3-hydroxyphenyl)-1H-benzimidazol-5-ol
  参考文献：
  名称：

  Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives

  摘要：

  A series of 2-arylbenzimidazole derivatives (3a-3p and 4a-4i) were synthesized and evaluated as potential antioxidant and antimicrobial agents. Their antioxidant properties were evaluated by various in vitro assays including hydroxyl radical (HO center dot) scavenging, superoxide radical anion (O-2(center dot)) scavenging, 1,1-diphenyl- 2-picrylhydrazyl (DPPH) radical scavenging, and ferric reducing antioxidant power. Results demonstrated that compounds with hydroxyl group at the 5-position of benzimidazole ring had a comparable or better antioxidant activity in comparison to standard antioxidant tert-butylhydroquinone (TBHQ). Markedly, compound 4h that showed the highest HO center dot scavenging activity (EC50 = 46 mu M) in vitro had a significant reduction of 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH)-induced intracellular oxidative stress and H2O2-induced cell death. In addition, these compounds showed moderate to good inhibitory activity against Staphylococcus aureus selectively at noncytotoxic concentrations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.05.004

文献信息

• Synthesis, antioxidant, and antimicrobial evaluation of some 2-arylbenzimidazole derivatives
  作者：Binhua Zhou、Baojian Li、Wei Yi、Xianzhang Bu、Lin Ma

  DOI：10.1016/j.bmcl.2013.05.004

  日期：2013.7

  A series of 2-arylbenzimidazole derivatives (3a-3p and 4a-4i) were synthesized and evaluated as potential antioxidant and antimicrobial agents. Their antioxidant properties were evaluated by various in vitro assays including hydroxyl radical (HO center dot) scavenging, superoxide radical anion (O-2(center dot)) scavenging, 1,1-diphenyl- 2-picrylhydrazyl (DPPH) radical scavenging, and ferric reducing antioxidant power. Results demonstrated that compounds with hydroxyl group at the 5-position of benzimidazole ring had a comparable or better antioxidant activity in comparison to standard antioxidant tert-butylhydroquinone (TBHQ). Markedly, compound 4h that showed the highest HO center dot scavenging activity (EC50 = 46 mu M) in vitro had a significant reduction of 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH)-induced intracellular oxidative stress and H2O2-induced cell death. In addition, these compounds showed moderate to good inhibitory activity against Staphylococcus aureus selectively at noncytotoxic concentrations. (C) 2013 Elsevier Ltd. All rights reserved.