2-[[4-[(2-Hydroxyphenyl)methylideneamino]-1,5-dimethyl-2-phenylpyrazol-3-ylidene]amino]benzoic acid | 1351988-01-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[[4-[(2-Hydroxyphenyl)methylideneamino]-1,5-dimethyl-2-phenylpyrazol-3-ylidene]amino]benzoic acid
• CAS: 1351988-01-6
• 化学式: C₂₅H₂₂N₄O₃
• 分子量: 426.475
• InChiKey: FKFFBPCZGFRAFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  88.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[[4-[(2-Hydroxyphenyl)methylideneamino]-1,5-dimethyl-2-phenylpyrazol-3-ylidene]amino]benzoic acid 、 zinc(II) chloride 以 乙醇 为溶剂， 以72%的产率得到
  参考文献：
  名称：

  Exploring the DNA binding mode of transition metal based biologically active compounds

  摘要：

  Few novel 4-aminoantipyrine derived Schiff bases and their metal complexes were synthesized and characterized. Their structural features and other properties were deduced from the elemental analysis, magnetic susceptibility and molar conductivity as well as from mass, IR, UV-vis, (1)H NMR and EPR spectral studies. The binding of the complexes with CT-DNA was analyzed by electronic absorption spectroscopy, viscosity measurement, and cyclic voltammetry. The interaction of the metal complexes with DNA was also studied by molecular modeling with special reference to docking. The experimental and docking results revealed that the complexes have the ability of interaction with DNA of minor groove binding mode. The intrinsic binding constants (K(b)) of the complexes with CT-DNA were found out which show that they are minor groove binders. Gel electrophoresis assay demonstrated the ability of the complexes to cleave the pUC19 DNA in the presence of AH(2) (ascorbic acid). Moreover, the oxidative cleavage studies using distamycin revealed the minor groove binding for the newly synthesized 4-aminoantipyrine derived Schiff bases and their metal complexes. Evaluation of antibacterial activity of the complexes against Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Staphylococcus epidermidis, and Klebsiella pneumoniae exhibited that the complexes have potent biocidal activity than the free ligands.

  DOI：

  10.1016/j.saa.2011.09.065
• 作为产物：
  描述：

  4-氨基安替比林 、 水杨醛 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 2-[[4-[(2-Hydroxyphenyl)methylideneamino]-1,5-dimethyl-2-phenylpyrazol-3-ylidene]amino]benzoic acid
  参考文献：
  名称：

  Exploring the DNA binding mode of transition metal based biologically active compounds

  摘要：

  Few novel 4-aminoantipyrine derived Schiff bases and their metal complexes were synthesized and characterized. Their structural features and other properties were deduced from the elemental analysis, magnetic susceptibility and molar conductivity as well as from mass, IR, UV-vis, (1)H NMR and EPR spectral studies. The binding of the complexes with CT-DNA was analyzed by electronic absorption spectroscopy, viscosity measurement, and cyclic voltammetry. The interaction of the metal complexes with DNA was also studied by molecular modeling with special reference to docking. The experimental and docking results revealed that the complexes have the ability of interaction with DNA of minor groove binding mode. The intrinsic binding constants (K(b)) of the complexes with CT-DNA were found out which show that they are minor groove binders. Gel electrophoresis assay demonstrated the ability of the complexes to cleave the pUC19 DNA in the presence of AH(2) (ascorbic acid). Moreover, the oxidative cleavage studies using distamycin revealed the minor groove binding for the newly synthesized 4-aminoantipyrine derived Schiff bases and their metal complexes. Evaluation of antibacterial activity of the complexes against Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Staphylococcus epidermidis, and Klebsiella pneumoniae exhibited that the complexes have potent biocidal activity than the free ligands.

  DOI：

  10.1016/j.saa.2011.09.065