3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol | 303769-54-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol
• 英文别名: 3-[(3,5-Dimethylphenyl)iminomethyl]benzene-1,2-diol
• CAS: 303769-54-2
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: NNDPCBXVVWJLIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3,5-二羟基苯甲醛 、 1-氨基-3,5-二甲苯 以 甲苯 为溶剂， 以85%的产率得到3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol
  参考文献：
  名称：

  Synthesis, characterization, biological screenings and interaction with calf thymus DNA of a novel azomethine 3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol

  摘要：

  The novel azomethine, 3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol (HL) was synthesized and characterized by elemental analysis, FT-IR, H-1, C-13 NMR spectroscopy and single crystal analysis. The title compound has been screened for its biological activities including enzymatic study, antibacterial, antifungal, cytotoxicity, antioxidant and interaction with CTDNA, and showed remarkable activities in each area of research. The titled compound interacts with DNA via two binding modes: intercalation and groove binding. In intercalation the compound inserts itself into the base pairs of DNA and the compound-DNA complex is stabilized by pi-pi stacking. Interaction via groove binding may be due to hydrogen bonding to bases, typically to N3 of adenine and O2 of thymine. The synthesized compound was also found to be an effective antioxidant of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) and gives percent inhibition (%I) of 90.7 at a concentration level of 31.3 mu g/mL. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.03.068
• 作为试剂：
  描述：

  磷酸单硝基苯基酯 在 3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol 作用下， 以 二甲基亚砜 为溶剂， 生成 对硝基苯酚
  参考文献：
  名称：

  Synthesis, characterization, biological screenings and interaction with calf thymus DNA of a novel azomethine 3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol

  摘要：

  The novel azomethine, 3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol (HL) was synthesized and characterized by elemental analysis, FT-IR, H-1, C-13 NMR spectroscopy and single crystal analysis. The title compound has been screened for its biological activities including enzymatic study, antibacterial, antifungal, cytotoxicity, antioxidant and interaction with CTDNA, and showed remarkable activities in each area of research. The titled compound interacts with DNA via two binding modes: intercalation and groove binding. In intercalation the compound inserts itself into the base pairs of DNA and the compound-DNA complex is stabilized by pi-pi stacking. Interaction via groove binding may be due to hydrogen bonding to bases, typically to N3 of adenine and O2 of thymine. The synthesized compound was also found to be an effective antioxidant of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) and gives percent inhibition (%I) of 90.7 at a concentration level of 31.3 mu g/mL. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2012.03.068

文献信息

• Synthesis, characterization, biological screenings and interaction with calf thymus DNA of a novel azomethine 3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol
  作者：Muhammad Sirajuddin、Saqib Ali、Naseer Ali Shah、Muhammad Rashid Khan、Muhammad Nawaz Tahir

  DOI：10.1016/j.saa.2012.03.068

  日期：2012.8

  The novel azomethine, 3-((3,5-dimethylphenylimino)methyl)benzene-1,2-diol (HL) was synthesized and characterized by elemental analysis, FT-IR, H-1, C-13 NMR spectroscopy and single crystal analysis. The title compound has been screened for its biological activities including enzymatic study, antibacterial, antifungal, cytotoxicity, antioxidant and interaction with CTDNA, and showed remarkable activities in each area of research. The titled compound interacts with DNA via two binding modes: intercalation and groove binding. In intercalation the compound inserts itself into the base pairs of DNA and the compound-DNA complex is stabilized by pi-pi stacking. Interaction via groove binding may be due to hydrogen bonding to bases, typically to N3 of adenine and O2 of thymine. The synthesized compound was also found to be an effective antioxidant of 2,2-diphenyl-1-picrylhydrazyl radical (DPPH) and gives percent inhibition (%I) of 90.7 at a concentration level of 31.3 mu g/mL. (C) 2012 Elsevier B.V. All rights reserved.