6,8-dichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester | 31601-83-9

• 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: 6,8-dichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
• 英文别名: ethyl 6,8-dichloro-4-oxo-1H-quinoline-3-carboxylate
• CAS: 31601-83-9
• 化学式: C₁₂H₉Cl₂NO₃
• mdl: MFCD06093748
• 分子量: 286.114
• InChiKey: HFSJXUVDOXWRGT-UHFFFAOYSA-N

物化性质

• 沸点：
  412.3±45.0 °C(Predicted)
• 密度：
  1.444±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,8-dichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 76.0h， 生成 N-(1-adamantanyl)-6,8-dichloro-4-oxo-1,4-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  作为抗结核药物的新型芳基甲酰胺衍生物的设计、合成和生物学评价

  摘要：

  我们小组之前曾报道过几种表现出强效抗结核活性的吲哚甲酰胺。在这里，我们基于我们之前报道的同源模型和最近发表的分枝杆菌膜蛋白大 3 (MmpL3) 的晶体结构合理地设计了几种芳基甲酰胺。许多类似物对药物敏感 (DS)结核分枝杆菌( M. tb ) 菌株表现出相当大的抗结核活性。萘酰胺衍生物13c和13d是我们研究中最活跃的化合物（MIC：分别为 6.55、7.11 μM），显示出与一线抗结核（抗 TB）药物乙胺丁醇（MIC：4.89 μM）相当的效力。除了萘酰胺衍生物外，我们还确定了喹诺酮-2-甲酰胺和 4-芳基噻唑-2-甲酰胺作为潜在的 MmpL3 抑制剂，其中化合物8i和18b的 MIC 值分别为 9.97 和 9.82 μM。所有四种化合物都保留了对多重耐药 (MDR) 和广泛耐药 (XDR)结核分枝杆菌菌株的高活性。值得注意的是，两种活性最高的化合物13c和13d对 DS、MDR 和

  DOI：

  10.1039/c9ra10663d
• 作为产物：
  描述：

  2,4-二氯苯胺 在 二苯醚 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 6,8-dichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
  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

文献信息

• Dichloro-4-quinolinol-3-carboxylic acid: Synthesis and antioxidant abilities to scavenge radicals and to protect methyl linoleate and DNA
  作者：Guo-Xiang Li、Zai-Qun Liu、Xu-Yang Luo

  DOI：10.1016/j.ejmech.2010.01.018

  日期：2010.5

  5,7-, 5,8-, 6,8-, 7,8-Dichloro-4-quinolinol-3-carboxylic acid (5,7-, 5,8-, 6,8-, 7,8-DCQA) together with 7-chloro-4-quinolinol-3-carboxylic acid (7-CQA) and 4-quinolinol-3-carboxylic acid (QA) were synthesized to investigate the antioxidant properties. 5,7-DCQA exhibited the highest ability to scavenge 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS+.), 2,2′-diphenyl-1-picrylhydrazyl

  5,7-，5,8-，6,8-，7,8-二氯-4-喹啉醇-3-羧酸（5,7-，5,8-，6,8-，7,8-DCQA ）与7-氯-4-喹啉-3-羧酸（7-CQA）和4-喹啉-3-羧酸（QA）一起合成以研究其抗氧化性能。5,7-DCQA表现出最高的清除2,2'-叠氮基双（3-乙基苯并噻唑啉-6-磺酸盐）阳离子自由基（ABTS +。），2,2'-二苯基-1-吡啶并肼基（DPPH）和加尔维氧基自由基的能力。6,8-DCQA具有最高的保护亚油酸甲酯抵抗2,2'-偶氮双（2-ami基丙烷）二盐酸盐（AAPH）诱导的氧化的功效。5,7-，5,8- DCQA和QA能够延缓β胡萝卜素漂在β-胡萝卜素-亚油酸乳液。此外，5,8-和6,8-DCQA有效保护DNA免受羟基自由基（.OH）介导的氧化作用，而5,8-DCQA和7-CQA具有保护DNA免受AAPH诱导的氧化作用的活性。此外，只有7-CQA可以保护DNA免受Cu
• Evaluation of 3-Carboxy-4(1<i>H</i>)-quinolones as Inhibitors of Human Protein Kinase CK2
  作者：Andriy G. Golub、Olexander Ya. Yakovenko、Volodymyr G. Bdzhola、Vladislav M. Sapelkin、Piotr Zien、Sergiy M. Yarmoluk

  DOI：10.1021/jm050048t

  日期：2006.11.1

  Due to the emerging role of protein kinase CK2 as a molecule that participates not only in the development of some cancers but also in viral infections and inflammatory failures, small organic inhibitors of CK2, besides application in scientific research, may have therapeutic significance. In this paper, we present a new class of CK2 inhibitorss3-carboxy-4(1H)-quinolones. This class of inhibitors has been selected via receptor-based virtual screening of the Otava compound library. It was revealed that the most active compounds, 5,6,8-trichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7) (IC50 = 0.3 mu M) and 4-oxo-1,4-dihydrobenzo[h] quinoline-3-carboxylic acid (9) (IC50 = 1 AM), are ATP competitive (K-i values are 0.06 and 0.28 mu M, respectively). Evaluation of the inhibitors on seven protein kinases shows considerable selectivity toward CK2. According to theoretical calculations and experimental data, a structural model describing the key features of 3-carboxy-4(1H)-quinolones responsible for tight binding to CK2 active site has been developed.
• An NMR Study of Halogenated 1,4-Dihydro-1-ethyl-4-oxoquinoline-3-carboxylates
  作者：B. Podányi、G. Keresztúri、L. Vasvári-Debreczy、I. Hermecz、G. Tóth

  DOI：10.1002/(sici)1097-458x(199611)34:11<972::aid-omr994>3.0.co;2-9

  日期：1996.11

  Ethyl 1,4-dihydro-1-ethyl-4-oxoquinoline-3-carboxylate and 29 of its mono-, di- and tri-fluoro and/or -chloro derivatives were synthesized and their H-1, C-13 and F-19 NMR spectra were recorded. H-1,C-13 and F-19 chemical shifts, J(HH), J(FH), J(CF) and J(FF) coupling constants are reported. The C-13 substituent chemical shift values of the chloro and fluoro substituents were calculated by linear multiple regression.
• 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.
• 4-Hydroxy-2-quinolenes. 20.* Synthesis and chemical conversions of ehtyl esters of the chloro-substituted quinoline-3-carboxylic acids
  作者：I. V. Ukrainets、S. G. Taran、O. V. Gorokhova、N. A. Marusenko、S. N. Kovalenko、A. V. Turov、N. I. Filimonova、S. M. Ivkov

  DOI：10.1007/bf01169674

  日期：1995.2