9-fluoro-N'-[(E/Z)-(2-hydroxyphenyl)methylidene]-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carbohydrazide | 1315249-13-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9-fluoro-N'-[(E/Z)-(2-hydroxyphenyl)methylidene]-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carbohydrazide
• 英文别名: 9-fluoro-3,7-dihydro-3-methyl l-6-(2-hydroxy-N'-methylenebenzohydrazide)10-(4-methylpiperazin-1-yl)-2H-[1,4]oxazino[2,3,4-ij]quinolin-7-one；9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1.2.3-de]-1,4-benzoxazine-6-carbaldehydebenzoyl hydrazone
• CAS: 1315249-13-8
• 化学式: C₂₅H₂₆FN₅O₄
• 分子量: 479.511
• InChiKey: USGYZDXGGWJJNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.32
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  99.4
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 neodymium(III) nitrate hexahydrate 、 9-fluoro-N'-[(E/Z)-(2-hydroxyphenyl)methylidene]-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carbohydrazide 在 NaOH 作用下， 以 甲醇 为溶剂， 以78%的产率得到
  参考文献：
  名称：

  Crystal structure, biological studies of water-soluble rare earth metal complexes with an ofloxacin derivative

  摘要：

  Two new water-soluble solid complexes [PrL (NO3)(2)(CH3OH)] (NO3), [NdL(NO3)(2)(CH3OH)](NO3)(L = 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperaziny)-7-oxo-7H-pyrido [1,2,3-de]-1,4-benzoxazine-6-carbaldehyde benzoyl hydrazone) have been synthesized by the reaction of Ln(III) nitrate with an ofloxacin derivative. The crystal structures of [PrL(NO3)(2)(CH3OH)](NO3) and [NdL(NO3)(2) (CH3OH)](NO3) were determined by single-crystal X-ray diffraction. The interactions of the ligand and Ln(III) complexes with calf thymus DNA (CT DNA) have been investigated by UV-Vis (UV-Vis) spectra, ethidium bromide (EB) displacement experiments, circular dichroism (CD) spectra, cyclic voltammetry (CV) and viscosity measurements. Experimental results indicated that Ln(III) complexes and ligand could bind to CT DNA via the intercalation mode and that the binding affinities of Ln(III) complexes are higher than that of free ligand. In addition, Ln(III) complexes could cleave pBR322 DNA in the presence and the absence of reductant. The free ligand did not show any DNA-cleaving abilities. Furthermore, the antioxidant activity of the ligand and Ln(III) complexes was determined by superoxide and hydroxyl radical scavenging methods in vitro, which indicate that the Ln(III) complexes exhibit more effective antioxidant activity than the ligand alone. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.12.031
• 作为产物：
  描述：

  氧氟沙星 在 硫酸 、 一水合肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 27.0h， 生成 9-fluoro-N'-[(E/Z)-(2-hydroxyphenyl)methylidene]-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carbohydrazide
  参考文献：
  名称：

  Crystal structure, biological studies of water-soluble rare earth metal complexes with an ofloxacin derivative

  摘要：

  Two new water-soluble solid complexes [PrL (NO3)(2)(CH3OH)] (NO3), [NdL(NO3)(2)(CH3OH)](NO3)(L = 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperaziny)-7-oxo-7H-pyrido [1,2,3-de]-1,4-benzoxazine-6-carbaldehyde benzoyl hydrazone) have been synthesized by the reaction of Ln(III) nitrate with an ofloxacin derivative. The crystal structures of [PrL(NO3)(2)(CH3OH)](NO3) and [NdL(NO3)(2) (CH3OH)](NO3) were determined by single-crystal X-ray diffraction. The interactions of the ligand and Ln(III) complexes with calf thymus DNA (CT DNA) have been investigated by UV-Vis (UV-Vis) spectra, ethidium bromide (EB) displacement experiments, circular dichroism (CD) spectra, cyclic voltammetry (CV) and viscosity measurements. Experimental results indicated that Ln(III) complexes and ligand could bind to CT DNA via the intercalation mode and that the binding affinities of Ln(III) complexes are higher than that of free ligand. In addition, Ln(III) complexes could cleave pBR322 DNA in the presence and the absence of reductant. The free ligand did not show any DNA-cleaving abilities. Furthermore, the antioxidant activity of the ligand and Ln(III) complexes was determined by superoxide and hydroxyl radical scavenging methods in vitro, which indicate that the Ln(III) complexes exhibit more effective antioxidant activity than the ligand alone. (C) 2011 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2011.12.031

文献信息

• Design, synthesis, and docking studies of novel ofloxacin analogues as antimicrobial agents
  作者：S. Jubie、P. Prabitha、R. Rajesh Kumar、R. Kalirajan、R. Gayathri、S. Sankar、K. Elango

  DOI：10.1007/s00044-011-9655-8

  日期：2012.7

  A number of novel ofloxacin analogues were synthesized by modifying the carboxylic acid at C-6. To investigate the antimicrobial data on structural basis, in-silico docking studies of the tested compounds into the crystal structure of topoisomerase II using Autodock vina 4.0 program was performed in order to predict the affinity and orientation of the synthesized compounds at the activities. R (2) values show good agreement with predicted binding affinities obtained by molecular docking studies. Also, it is verified by in-vitro antimicrobial screening, where all the compounds were most active against Staphylococcus aureus, Staphylococcus epidermidis and Bacillus subtilis. Among these compounds 3a, 3b, 3f showed good MIC (0.125 mu g/ml).
• Dündar, Yasemin; Ülger, Mahmut; Kaynak Onurdağ, Fatma, Revue Roumaine de Chimie, 2018, vol. 63, # 4, p. 265 - 272
  作者：Dündar, Yasemin、Ülger, Mahmut、Kaynak Onurdağ, Fatma、Ökten, Suzan、Önkol, Tijen

  DOI：——

  日期：——