ethyl 6-fluoro-1-(oxiran-2-ylmethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate | 1435910-85-2

• 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: ethyl 6-fluoro-1-(oxiran-2-ylmethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
• 英文别名: Ethyl 6-fluoro-1-(oxiran-2-ylmethyl)-4-oxoquinoline-3-carboxylate；ethyl 6-fluoro-1-(oxiran-2-ylmethyl)-4-oxoquinoline-3-carboxylate
• CAS: 1435910-85-2
• 化学式: C₁₅H₁₄FNO₄
• 分子量: 291.279
• InChiKey: NDJZCUCMBZYPEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 6-fluoro-1-(oxiran-2-ylmethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate 在 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.5h， 生成 6-fluoro-1-(2-hydroxy-3-(4-nitro-1H-imidazol-1-yl)propyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid
  参考文献：
  名称：

  甲硝唑和喹诺酮类的新型杂种：合成，生物活性评估，细胞毒性，初步抗菌机制以及金属离子对人血清白蛋白转运的影响

  摘要：

  设计并合成了一系列新型的甲硝唑和喹诺酮类抗微生物剂。与参考药物相比，大多数制备的化合物表现出良好或什至更强的抗菌活性。此外，这些高活性甲硝唑-喹诺酮杂种对药代动力学表现出适当的pKa，log P和水溶解度范围，对A549和人肝细胞LO2细胞无明显毒性。它们与金属离子对HSA的竞争性相互作用表明，Mg 2+离子参与化合物7d -HSA缔合可能导致游离化合物7d的浓度增加。化合物7d的分子建模和实验研究 DNA提示可能的抗菌机制可能与生物活性分子和topo IV-DNA复合物之间的多个结合位点有关。

  DOI：

  10.1016/j.ejmech.2014.08.063
• 作为产物：
  描述：

  (4-氟苯基氨基)亚甲基丙二酸二乙酯 在 potassium carbonate 作用下， 以 二苯醚 为溶剂， 反应 4.0h， 生成 ethyl 6-fluoro-1-(oxiran-2-ylmethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of a class of quinolone triazoles as potential antimicrobial agents and their interactions with calf thymus DNA

  摘要：

  A novel series of quinolone triazoles were synthesized and characterized by IR, NMR, MS and HRMS spectra. All the newly prepared compounds were screened for their antimicrobial activities against seven bacteria and four fungi. Bioactive assay manifested that most of new compounds exhibited good or even stronger antibacterial and antifungal activities against the tested strains including multi-drug resistant MRSA in comparison with reference drugs Norfloxacin, Chloromycin and Fluconazole. The preliminary interactive investigations of compound 6b with calf thymus DNA by fluorescence and UV-vis spectroscopic methods revealed that compound 6b could effectively intercalate DNA to form compound 6b-DNA complex which might block DNA replication and thus exert its antimicrobial activities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.118

文献信息

• Novel hybrids of metronidazole and quinolones: Synthesis, bioactive evaluation, cytotoxicity, preliminary antimicrobial mechanism and effect of metal ions on their transportation by human serum albumin
  作者：Sheng-Feng Cui、Li-Ping Peng、Hui-Zhen Zhang、Syed Rasheed、Kannekanti Vijaya Kumar、Cheng-He Zhou

  DOI：10.1016/j.ejmech.2014.08.063

  日期：2014.10

  A novel series of hybrids of metronidazole and quinolones as antimicrobial agents were designed and synthesized. Most prepared compounds exhibited good or even stronger antimicrobial activities in comparison with reference drugs. Furthermore, these highly active metronidazole–quinolone hybrids showed appropriate ranges of pKa, log P and aqueous solubility to pharmacokinetic behaviors and no obvious

  设计并合成了一系列新型的甲硝唑和喹诺酮类抗微生物剂。与参考药物相比，大多数制备的化合物表现出良好或什至更强的抗菌活性。此外，这些高活性甲硝唑-喹诺酮杂种对药代动力学表现出适当的pKa，log P和水溶解度范围，对A549和人肝细胞LO2细胞无明显毒性。它们与金属离子对HSA的竞争性相互作用表明，Mg 2+离子参与化合物7d -HSA缔合可能导致游离化合物7d的浓度增加。化合物7d的分子建模和实验研究 DNA提示可能的抗菌机制可能与生物活性分子和topo IV-DNA复合物之间的多个结合位点有关。
• Synthesis and biological evaluation of a class of quinolone triazoles as potential antimicrobial agents and their interactions with calf thymus DNA
  作者：Sheng-Feng Cui、Yu Ren、Shao-Lin Zhang、Xin-Mei Peng、Guri L.V. Damu、Rong-Xia Geng、Cheng-He Zhou

  DOI：10.1016/j.bmcl.2013.03.118

  日期：2013.6

  A novel series of quinolone triazoles were synthesized and characterized by IR, NMR, MS and HRMS spectra. All the newly prepared compounds were screened for their antimicrobial activities against seven bacteria and four fungi. Bioactive assay manifested that most of new compounds exhibited good or even stronger antibacterial and antifungal activities against the tested strains including multi-drug resistant MRSA in comparison with reference drugs Norfloxacin, Chloromycin and Fluconazole. The preliminary interactive investigations of compound 6b with calf thymus DNA by fluorescence and UV-vis spectroscopic methods revealed that compound 6b could effectively intercalate DNA to form compound 6b-DNA complex which might block DNA replication and thus exert its antimicrobial activities. (C) 2013 Elsevier Ltd. All rights reserved.