ofloxacine ethyl ester | 107884-32-2

• 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: ofloxacine ethyl ester
• 英文别名: 9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperaziny)-7-oxo-7H-pyrido [1,2,3-de]-1,4-benzoxazine-6-carboxylate；ethyl (+/-)-9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-1,4-benzoxazine-6-carboxylate；ethyl 9-fluoro-3,7-dihydro-3-methyl-10-(4-methylpiperazin-yl)-7-oxo-2H-[1,4]oxazino[2,3,4-ij]quinolone-6-carboxylate；Ethyl 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate；ethyl 7-fluoro-2-methyl-6-(4-methylpiperazin-1-yl)-10-oxo-4-oxa-1-azatricyclo[7.3.1.05,13]trideca-5(13),6,8,11-tetraene-11-carboxylate
• CAS: 107884-32-2
• 化学式: C₂₀H₂₄FN₃O₄
• 分子量: 389.427
• InChiKey: OEHYGCZCGGEXKX-UHFFFAOYSA-N

物化性质

• 熔点：
  238-240 °C
• 沸点：
  559.6±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  62.3
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ofloxacine ethyl ester 在 一水合肼 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 9-fluoro-2,3-dihydro-6-(4,5-dihydro-4-(3-oxo-3-phenylpropyl)-5-sulfanylene-1,3,4-oxadiazol-2-yl)-3-methyl-l,10-(4-methylpiperazin-1-yl)-[1,4]oxazine[2,3,4-ij]quinolin-7-one
  参考文献：
  名称：

  Design, synthesis, and docking studies of novel ofloxacin analogues as antimicrobial agents

  摘要：

  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).

  DOI：

  10.1007/s00044-011-9655-8
• 作为产物：
  描述：

  2,3,5-三氟-4-(4-甲基-1-哌嗪基)-beta-氧代-苯丙酸 生成 ofloxacine ethyl ester
  参考文献：
  名称：

  EHGAVA, XIROSI;MIYAMOTO, AKIYUKI;MATSUMOTO, DZYUNITI

  摘要：

  DOI：

文献信息

• Characteristic and complementary chiral recognition ability of four recently developed immobilized chiral stationary phases based on amylose and cellulose phenyl carbamates and benzoates
  作者：Takafumi Onishi、Takunori Ueda、Kenichi Yoshida、Kosuke Uosaki、Hiroyuki Ando、Ryota Hamasaki、Atsushi Ohnishi

  DOI：10.1002/chir.23446

  日期：2022.7

  various immobilized chiral stationary phases (CSPs) have been developed. The immobilized CSPs have opened up possibilities not only maintaining the high chiral recognition abilities as well as corresponding coated ones but also affording high durability to various mobile phase. This report directed to investigate enantioseparation of recently launched four immobilized CSPs with cellulose and amylose

  迄今为止，已经开发了各种固定化手性固定相 (CSP)。固定化的 CSP 不仅为保持高手性识别能力和相应的涂层能力开辟了可能性，而且为各种流动相提供了高耐久性。本报告旨在研究在正相液相色谱条件下最近推出的四种具有纤维素和直链淀粉骨架的固定化 CSP 的对映体分离。将它们的手性识别能力与之前开发的六种固定化 CSP 进行了比较。特别是，我们专注于手性识别的互补性。其中，直链淀粉三（3-氯-5-甲基苯基氨基甲酸酯）CSP，即CHIRALPAK IG，对各种外消旋体显示出显着的手性识别能力。正如预期的那样，研究的固定化 CSP 对各种流动相具有显着的耐久性，而相应的涂层 CSP 由于不可逆的降解而无法运行。利用不受限制的溶剂相容性，一些外消旋体的手性分离选择性得到改善。
• Spectroscopic studies on the interaction between Pr(III) complex of an ofloxacin derivative and bovine serum albumin or DNA
  作者：Min Xu、Zhao-Rong Ma、Liang Huang、Feng-Juan Chen、Zheng-zhi Zeng

  DOI：10.1016/j.saa.2010.11.018

  日期：2011.1

  The binding properties on [PrL2(NO3)](NO3)(2) (L=9-fluoro-2,3-dihydro-3-methyl-10-(4-methyl-1-piperaziny)-7-oxo-7Hpyrido[1,2,3-de]-1,4-benzoxazine-6-carbaldehyde benzoyl hydrazone) to bovine serum albumin (BSA) have been studied for the first time using fluorescence spectroscopy in combination with UV-Vis absorbance spectroscopy. The results showed that [PrL2(NO3)](NO3)(2) strongly quenched the intrinsic fluorescence of BSA through a static quenching procedure, and non-radiation energy transfer happened within molecules. The number of binding site was about 1, and the efficiency of Forster energy transfer provided a distance of 4.26 nm between tryptophan and [PrL2(NO3)](NO3)(2) binding site. At 288, 298, 310K, the quenching constants of BSA-(PrL2(NO3)](NO3)(2) system were 5.11 x 10(4), 4.33 x 10(4) and 3.71 x 10(4) IM-1. Delta H, Delta S and Delta G were obtained based on the quenching constants and thermodynamic theory (Delta H < 0, Delta S> 0 and Delta G<0). These results indicated that hydrophobic and electrostatic interactions are the mainly binding forces in the [PrL2(NO3)](NO3)(2)-BSA system. In addition, the CD spectra have proved that BSA secondary structure changed in the presence of [PrL2(NO3)](NO3)(2) in aqueous solution. Moreover, the interaction between [PrL2(NO3)](NO3)(2) and calf thymus DNA (CT DNA) was studied by spectroscopy and viscosity measurements, which showed that the binding mode of the [PrL2(NO3)](NO3)(2) with DNA is intercalation. The DNA cleavage results show that in the absence of any reducing agent, the [PrL2(NO3)](NO3)(2) can cleave plasmid pBR322 DNA and its hydrolytic mechanism was demonstrated with hydroxyl radical scavengers and singlet oxygen quenchers. (C) 2010 Elsevier B.V. All rights reserved.
• Crystal structure, biological studies of water-soluble rare earth metal complexes with an ofloxacin derivative
  作者：Min Xu、Yu-cui Zhang、Zhi-hong Xu、Zheng-zhi Zeng

  DOI：10.1016/j.ica.2011.12.031

  日期：2012.4

  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.
• EGAWA HIROSHI; MIYAMOTO TERUYUKI; MATSUMOTO JUN-ICHI, CHEM. AND PHARM. BULL., 34,(1986) N 10, 4098-4102
  作者：EGAWA HIROSHI、 MIYAMOTO TERUYUKI、 MATSUMOTO JUN-ICHI

  DOI：——

  日期：——
• 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).