1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | 3832-97-1

• 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: 1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• 英文别名: 1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid；1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid
• CAS: 3832-97-1
• 化学式: C₁₂H₁₀FNO₃
• mdl: MFCD00784834
• 分子量: 235.215
• InChiKey: MGJXIOXOKWLZFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carbonyl chloride
  参考文献：
  名称：

  一种具有喹诺酮和β-内酰胺结构的化合物及其合成方法

  摘要：

  本发明提供一种具有喹诺酮和β?内酰胺结构的化合物及其合成方法，所述该类化合物的分子结构如下：6?(1?乙基?6?氟?4?氧代?1，4?二氢喹啉?3?甲酰胺基)?3，3?二甲基?7?氧代?4?硫杂?1?氮杂双环[3.2.0]庚烷?2?羧酸。本发明合成了一种既具有喹诺酮的基本结构，又具有β?内酰胺抗生素结构的新型化合物。

  公开号：

  CN105753887A
• 作为产物：
  描述：

  ethyl 1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate 在 水 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以95%的产率得到1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Bacterial patterning controlled by light exposure

  摘要：

  在一个系统中对多种细菌菌株进行图案化，是通过使用单一的光活化抗生素实现的。

  DOI：

  10.1039/c4ob02483d

文献信息

• Design, Synthesis and Evaluation of Novel Carbazole‐Derived Photocages
  作者：Zhipeng Wang、Stephen F. Martin

  DOI：10.1002/chem.202200311

  日期：2022.3.28

  the photochemical decaging efficiencies, ϵΦ, of the benzoates photocaged with NCARB and isoNCARB are about 150- and 20-fold better, respectively, at 400 nm than the corresponding caged benzoate derived from NDBF. The water solubility of molecules caged with nitrocarbazole analogs was improved by N-alkylation of NCARB, the better of the two new photocages, with an aminodicarboxylate group. This modified

  我们报告了两种新型光笼 NCARB 和 isoNCARB 的设计、合成和评估，它们属于邻硝基苄基化学型，基于咔唑环系统。这些异构封闭分子中的每一个的合成分五步完成，总产率为 29%，并使用苯甲酸作为封闭模型评估了它们的光化学性质。结果，在 400 nm 照射 60 分钟后，分别有 82% 和 42% 的苯甲酸从 NCARB 和 isoNCARB 光笼中释放出来，而只有 22% 的苯甲酸从硝基二苯并呋喃 (NDBF) 笼中释放出来。此外，在 400 nm 处，用 NCARB 和 isoNCARB 光笼的苯甲酸盐的光化学去笼效率 εΦ 分别比衍生自 NDBF 的相应笼状苯甲酸盐好约 150 倍和 20 倍。用硝基咔唑类似物笼罩的分子的水溶性通过 NCARB 的 N-烷基化得到改善，这两种新型光笼中较好的一个，具有氨基二羧酸酯基团。这种改良的笼子 NCARB-DA 被用于设计笼式氟喹诺酮类抗生素
• Antibacterial agents
  申请人：Warner-Lambert Company

  公开号：US04665079A1

  公开（公告）日：1987-05-12

  Novel naphthyridine-, quinoline- and benzoxazine-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

  本文介绍了新型萘啶基、喹啉基和苯并噁嗪基羧酸作为抗菌剂，以及它们的制备、配方和用于治疗细菌感染的方法，包括用于制备抗菌剂的某些新型中间体的描述。
• 7-(Pyridinyl)-/-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid having antibacterial activity and preparation thereof
  申请人：STERLING DRUG INC.

  公开号：EP0179239A2

  公开（公告）日：1986-04-30

  1-Ethyt-6-ftuoro-1,4-dihydro-7-(2,6-dimethy)-4-pyridinyt)-4-oxo-3-quinolinecarboxylic acid or salt thereof, a novel compound useful highly potent antibacterial agent with a broad spectrum of anti-microbial activity, is prepared by nitrating the corresponding 6-desfluoro compound to produce the corresponding 6-nitro compound, reducing the latter compound to produce the corresponding 6-amino compound and converting the 6-amino via its diazonium salt to said 6-fluoro compound. Said novel acid is also prepared via intermediates prepared by heating 4-(2-fluorophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid to produce a mixture of 4-(2-fluorophenyl)-2,6-di-methylpyridine and 2,4-dimethyl-5H-[1]benzopyrano[3,4-c)pyridin-5-one, separating the components of said mixture and nitrating 4-(2-fluorophenyl)-2,6-dimethylpyridine to produce 4-(2-fluoro-5-nitrophenyl)-2,6-dimethylpyridine.

  1-乙基-6-氟-1,4-二氢-7-(2,6-二甲基)-4-吡啶)-4-氧代-3-喹啉羧酸或其盐是一种新型化合物，是一种具有广谱抗微生物活性的高效抗菌剂、其制备方法是：硝化相应的 6-去氟化合物，生成相应的 6-硝基化合物；还原后者，生成相应的 6-氨基化合物；然后通过重氮盐将 6-氨基化合物转化为所述 6-氟化合物。所述新型酸也可以通过加热 4-(2-氟苯基)-2,6-二甲基-3,5-吡啶二羧酸生成 4-(2-氟苯基)-2,6-二甲基吡啶和 2、4-(2-氟苯基)-2,6-二甲基吡啶和 2,4-二甲基-5H-[1]苯并吡喃并[3,4-c]吡啶-5-酮的混合物，分离所述混合物的组分并硝化 4-(2-氟苯基)-2,6-二甲基吡啶，生成 4-(2-氟-5-硝基苯基)-2,6-二甲基吡啶。
• A Small-Molecule Inhibitor of Nipah Virus Envelope Protein-Mediated Membrane Fusion
  作者：Sabine Niedermeier、Katrin Singethan、Sebastian G. Rohrer、Magnus Matz、Markus Kossner、Sandra Diederich、Andrea Maisner、Jens Schmitz、Georg Hiltensperger、Knut Baumann、Ulrike Holzgrabe、Jürgen Schneider-Schaulies

  DOI：10.1021/jm900411s

  日期：2009.7.23

  Nipah virus (NiV), a highly pathogenic paramyxovirus. causes respiratory disease in pigs and severe febrile encephalitis in humans with high mortality rates. On the basis of the structural similarity of viral fusion (F) proteins within the family Paramyxoviridae, we designed and tested 18 quinolone derivatives in a NiV and measles virus (MV) envelope protein-based fusion assay beside evaluation of cytotoxicity. We found five compounds successfully inhibiting NiV envelope protein-induced cell fusion. The most active molecules (19 and 20), which also inhibit the syncytium formation induced by infectious NiV and show a low cytotoxicity in Vero cells, represent a promising lead quinolone-type compound structure. Molecular modeling indicated that compound 19 fits well into a particular protein cavity present on the NiV F protein that is important for the fusion process.
• Copper(II) complexes with new fluoroquinolones: Synthesis, structure, spectroscopic and theoretical study, DNA damage, cytotoxicity and antiviral activity
  作者：Sandra Dorotíková、Júlia Kožíšková、Michal Malček、Klaudia Jomová、Peter Herich、Kristína Plevová、Katarína Briestenská、Anna Chalupková、Jela Mistríková、Viktor Milata、Dana Dvoranová、Lukáš Bučinský

  DOI：10.1016/j.jinorgbio.2015.06.017

  日期：2015.9

  Copper(II) complexes with fluoroquinolones in the presence of the nitrogen donor heterocyclic ligands 1,10-phenanthroline have been considered in detail. The phenanthroline moiety was introduced into the ligand environment with the aim to determine whether the nuclease activity is feasible. All suitable X-ray structures of the complexes under study reveal a distorted square pyramidal coordination geometry for Cu(II) atom. The conformational and spectroscopic (FT-IR and UV-visible) behavior has been analyzed and has been interpreted with respect to B3LYP/6-311G* calculations including molecular dynamics. The ability of the complexes to cleave DNA was studied by agarose gel electrophoresis with plasmid DNA pBSK+. The results have confirmed that the complexes under study behave as the chemical nucleases. Nuclease like activity in the absence of hydrogen peroxide allows us to deduce an interaction of the complexes with the DNA resulting in the conversion of supercoiled circular DNA to the nicked form. The DNA cleavage activity enhanced by the presence of hydrogen peroxide demonstrates the participation of reactive oxygen species, such as superoxide radical anions and hydroxyl radicals which presence was confirmed independently using the standard radical scavenging agents. It has been suggested that the radical formation through the Fenton/Haber-Weiss reaction is mediated by the redox cycling mechanisms with the participation of cupric/cuprous ions. Cytotoxic activity was evaluated as the 50% cytotoxic concentration (CC50). The potential effects of tested compounds on replication of murine gammaherpesvirus 68 (MHV-68) under in vitro conditions were also evaluated. However, no antiviral activity against MHV-68 was observed. (C) 2015 Elsevier Inc. All rights reserved.