5-硝基-4(1H)-喹啉酮 | 23536-75-6

• 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
• 中文名称: 5-硝基-4(1H)-喹啉酮
• 中文别名: 5-硝基喹啉-4-醇
• 英文名称: 5-nitro-quinolin-4-ol
• 英文别名: 5-Nitro-chinolin-4-ol；4-Hydroxy-5-nitrochinolin；5-nitro-1H-quinolin-4-one
• CAS: 23536-75-6
• 化学式: C₉H₆N₂O₃
• mdl: MFCD09261098
• 分子量: 190.158
• InChiKey: BVZBDPJGFIMXLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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

安全信息

• 海关编码：
  2933499090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5-硝基喹啉	5-nitroquinoline	607-34-1	C9H6N2O2	174.159
  5-硝基喹啉1-氧化物	5-nitro-quinoline-1-oxide	7613-19-6	C9H6N2O3	190.158
  4-氯-5-硝基-喹啉	4-chloro-5-nitroquinoline	40106-98-7	C9H5ClN2O2	208.604

反应信息

• 作为产物：
  描述：

  4-氯喹啉 在 盐酸 、 硫酸 、 水 、 硝酸 作用下， 生成 5-硝基-4(1H)-喹啉酮
  参考文献：
  名称：

  Heterocyclic Basic Compounds. X. 4,8-Diaminoquinoline and Derivatives

  摘要：

  DOI：

  10.1021/ja01194a044

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。
• Assembly of 4-Aminoquinolines via Palladium Catalysis:  A Mild and Convenient Alternative to S_NAr Methodology
  作者：Brandon J. Margolis、Kimberly A. Long、Dana L. T. Laird、J. Craig Ruble、Shon R. Pulley

  DOI：10.1021/jo062168u

  日期：2007.3.1

  4-Aminoquinolines, classically prepared via SNAr chemistry from an amine and 4-haloquinoline, are important scaffolds in medicinal chemistry. Interest in these compounds prompted us to explore palladium catalysis as an alternative to the existing methods for their preparation. Initial results followed by an iterative screening paradigm confirmed Pd(OAc)(2)/ DPEphos/K3PO4 as a mild and convenient alternative for the formation of the C-N bond in 4-aminoquinolines. A description of the screen and the scope of this methodology are discussed herein.
• Synthesis and pharmacological evaluation of new cysLT1 receptor antagonists
  作者：R Griera、M Armengol、A Reyes、M Alvarez、A Palomer、F Cabré、J Pascual、M.L. Garcia、D Mauleón

  DOI：10.1016/s0223-5234(97)83282-5

  日期：1997.7

  This paper describes the synthesis and pharmacological evaluation of three series of compounds 4a-b, 13a-k and 19, structurally related to the known potent cysLT(1) receptor antagonists RG-12553, ICI-204219 and ONO-1078, respectively. The common structural feature of these new series is the presence of a 4-quinolone nucleus acting as a template for substitution of the aromatic nucleus present in the prototype antagonists. We describe the evolution of these series leading to antagonists with potency at nanomolar concentrations in vitro.
• Wetzel et al., Journal of the American Pharmaceutical Association (1912), 1946, vol. 35, p. 331,332
  作者：Wetzel et al.

  DOI：——

  日期：——