7-nitroquinolin-4(1H)-one | 75770-07-9

• 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: 7-nitroquinolin-4(1H)-one
• 英文别名: 7-nitro-4-quinolone；4-Hydroxy-7-nitroquinoline；7-nitro-1H-quinolin-4-one
• CAS: 75770-07-9
• 化学式: C₉H₆N₂O₃
• mdl: MFCD08688614
• 分子量: 190.158
• InChiKey: MLPKSYLYDHCVOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-nitroquinolin-4(1H)-one 在 三氯氧磷 作用下， 反应 1.0h， 生成 4-氯-7-硝基喹啉
  参考文献：
  名称：

  4-[(Quinolin-4-yl)amino]苯甲酰胺衍生物作为新型抗流感病毒药物的设计、合成、分子对接分析和生物学评价

  摘要：

  本研究设计合成了一系列4-[(quinolin-4-yl)amino]苯甲酰胺衍生物作为新型抗流感药物。进行细胞毒性试验、细胞病变效应试验和噬斑抑制试验以评估目标化合物的抗流感病毒 A/WSN/33 (H1N1) 活性。目标化合物G07在细胞病变效应试验 (EC 50 = 11.38 ± 1.89 µM) 和噬菌斑抑制试验 (IC 50 = 0.23 ± 0.15 µM)中均表现出显着的抗流感病毒 A/WSN/33 (H1N1) 活性。G07对其他三种不同的流感病毒株 A/PR/8 (H1N1)、A/HK/68 (H3N2) 和乙型流感病毒也表现出显着的抗流感病毒活性。根据核糖核蛋白重组试验结果，G07与核糖核蛋白相互作用良好，在100 µM时抑制率为80.65%。此外，根据最佳药效团 Hypo1 预测的 PA-PB1 抑制活性， G07表现出显着的活性靶标 RNA 聚合酶 PA-PB1

  DOI：

  10.3390/ijms23116307
• 作为产物：
  描述：

  二乙基(3-硝基苯胺亚甲基)丙二酸 在 水 、 sodium hydroxide 作用下， 以 二苯醚 为溶剂， 反应 7.6h， 生成 7-nitroquinolin-4(1H)-one
  参考文献：
  名称：

  4-[(Quinolin-4-yl)amino]苯甲酰胺衍生物作为新型抗流感病毒药物的设计、合成、分子对接分析和生物学评价

  摘要：

  本研究设计合成了一系列4-[(quinolin-4-yl)amino]苯甲酰胺衍生物作为新型抗流感药物。进行细胞毒性试验、细胞病变效应试验和噬斑抑制试验以评估目标化合物的抗流感病毒 A/WSN/33 (H1N1) 活性。目标化合物G07在细胞病变效应试验 (EC 50 = 11.38 ± 1.89 µM) 和噬菌斑抑制试验 (IC 50 = 0.23 ± 0.15 µM)中均表现出显着的抗流感病毒 A/WSN/33 (H1N1) 活性。G07对其他三种不同的流感病毒株 A/PR/8 (H1N1)、A/HK/68 (H3N2) 和乙型流感病毒也表现出显着的抗流感病毒活性。根据核糖核蛋白重组试验结果，G07与核糖核蛋白相互作用良好，在100 µM时抑制率为80.65%。此外，根据最佳药效团 Hypo1 预测的 PA-PB1 抑制活性， G07表现出显着的活性靶标 RNA 聚合酶 PA-PB1

  DOI：

  10.3390/ijms23116307

文献信息

• Synthesis and biological evaluation of new heterocyclic quinolinones as anti-parasite and anti-HIV drug candidates
  作者：Albert Darque、Aurélien Dumètre、Sébastien Hutter、Gilles Casano、Maxime Robin、Christophe Pannecouque、Nadine Azas

  DOI：10.1016/j.bmcl.2009.08.013

  日期：2009.10

  We have synthesized quinolinones with potential antiparasitic and anti-HIV activities by an original two-step method involving microwave irradiation and have evaluated their activities against Plasmodium falciparum, Leishmania donovani, Trichomonas vaginalis, and HIV. None of the tested compounds had been previously described using this method of synthesis. One of the compounds had interesting antiparasitic

  我们已经通过涉及微波辐射的原始两步法合成了具有潜在抗寄生虫和抗HIV活性的喹啉酮，并评估了它们对恶性疟原虫，杜氏利什曼原虫，阴道毛滴虫和HIV的活性。以前没有使用这种合成方法描述过测试化合物。其中一种化合物具有令人感兴趣的抗寄生虫和抗HIV活性，可以通过用不同的基团取代来提高其活性。
• Gas-Phase Pyrolysis in Organic Synthesis: Rapid Green Synthesis of 4-Quinolinones
  作者：Nouria Al-Awadi、Ismail Abdelhamid、Ismail Abdelhamid、Alya Al-Etaibi、Mohamed Elngadi

  DOI：10.1055/s-2007-985573

  日期：——

  Gas-phase pyrolysis of aminomethylene Meldrum’s acid derivatives gave quinolinones and/or amines depending on the -nature of arylamino moiety. Effect of substituent on reaction rate and nature of pyrolysis products supports the suggested intramolecular nucleophilic substitution reaction via initially formed keteneamine intermediate.

  根据芳基氨基部分的性质，氨基亚甲基 Meldrum 的酸衍生物的气相热解得到喹啉酮和/或胺。取代基对反应速率和热解产物性质的影响支持通过最初形成的烯酮胺中间体进行的分子内亲核取代反应。
• Method for the Fluorescent Detection of Nitroreductase Activity Using Nitro-Substituted Aromatic Compounds
  申请人：Smaill Jeffrey B.

  公开号：US20100173332A1

  公开（公告）日：2010-07-08

  A method utilising one or more fluorogenic probes, for the detection of nitroreductase activity. The non-fluorescent probes are reduced in the presence of nitroreductase to form fluorescent derivatives that may be detected using fluorescence spectroscopy. In particular, the method may be used to detect and/or identify a plurality of nitroreductase in a single test environment

  一种利用一个或多个荧光探针检测硝基还原酶活性的方法。非荧光探针在硝基还原酶存在下被还原成荧光衍生物，可以使用荧光光谱法检测。特别地，该方法可用于在单个测试环境中检测和/或鉴定多种硝基还原酶。
• Nitro and amino substituted topoisomerase agents
  申请人：——

  公开号：US20040102443A1

  公开（公告）日：2004-05-27

  The invention provides compounds of formula I: 1 wherein R 1 -R 9 , W, and X have any of the meanings defined in the specification and their pharmaceutically acceptable salts. The invention also provides pharmaceutical compositions. comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I, and therapeutic methods for treating cancer and infections using compounds of formula I.

  本发明提供了公式I的化合物：1其中R1-R9、W和X具有规范中定义的任何含义及其药学上可接受的盐。本发明还提供了包括公式I化合物的制药组合物，制备公式I化合物的过程，用于制备公式I化合物的中间体，以及使用公式I化合物治疗癌症和感染的治疗方法。
• Structure–activity relationships for ferriprotoporphyrin IX association and β-hematin inhibition by 4-aminoquinolines using experimental and ab initio methods
  作者：Samkele Nsumiwa、David Kuter、Sergio Wittlin、Kelly Chibale、Timothy J. Egan

  DOI：10.1016/j.bmc.2013.04.040

  日期：2013.7

  In order to probe structure-activity relationships of association with ferriprotoporphyrin IX (logK) and inhibition of beta-hematin formation, a series of 4-aminoquinolines with varying substituents at the 7-position (X) have been synthesized. These have been further elaborated by introduction of two different R groups on the 4-amino nitrogen atom in the form of methyl (R = Me) and ethylamine (R = EtNH2) side chains. Data for a previously investigated series containing an N,N-diethyl-ethylamine side chain were also compared with the findings of this study. Experimentally, logK values for the simple 4-aminoquinoline series (R = H) were found to correlate with the hydrophobicity constant (pi) of the group X. The logK values for the series with R = Me and EtNH2 were found to correlate with those of the series with R = H. The log of the 50% beta-hematin inhibitory activity (log BHIA(50)) was found to correlate with logK and either meta (sigma(m)) or para (sigma(p)) Hammett constants for the series with R = Me and EtNH2, but not the simple series with R = H. To further improve predictability, correlations with ab initio electrostatic parameters, namely Mulliken and CHelpG charges were investigated. The best correlations were found with CHelpG charges which indicated that logK values can be predicted from the charges on atom H-8 and the group X in the quinolinium species computed in vacuum, while log BHIA50 values can be predicted from the CHelpG charges on C-7, C-8 and N-1 for the neutral species in vacuum. These correlations indicate that association and inhibition of beta-hematin formation are separately determined. They also suggest that electron withdrawing groups at the 7-position, but not necessarily hydrophobic groups are required for hemozoin inhibition. The upshot is that the correlations imply that considerably more hydrophilic hemozoin inhibitors are feasible. (C) 2013 Elsevier Ltd. All rights reserved.