6-fluoro-4-hydroxy-3-propyl-2(1H)-quinolinone | 345913-48-6

• 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
• 英文名称: 6-fluoro-4-hydroxy-3-propyl-2(1H)-quinolinone
• 英文别名: 6-fluoro-4-hydroxy-3-propylquinolin-2(1H)-one；6-fluoro-4-hydroxyl-3-propyl-2(1H)-quinolinone；6-fluoro-4-hydroxy-3-propyl-1H-quinolin-2-one
• CAS: 345913-48-6
• 化学式: C₁₂H₁₂FNO₂
• 分子量: 221.231
• InChiKey: RFIXNVCNCNALLS-UHFFFAOYSA-N

物化性质

• 沸点：
  408.5±45.0 °C(Predicted)
• 密度：
  1.276±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-fluoro-4-hydroxy-3-propyl-2(1H)-quinolinone 以22%的产率得到4-cyclopentyloxy-6-fluoro-3-propyl-2(1H)-quinolinone
  参考文献：
  名称：

  Quinolone compounds for use in treating viral infections

  摘要：

  本发明涉及喹诺酮化合物及其在治疗病毒感染中的应用。

  公开号：

  US20030069271A1
• 作为产物：
  描述：

  4-氟苯胺 以56%的产率得到6-fluoro-4-hydroxy-3-propyl-2(1H)-quinolinone
  参考文献：
  名称：

  Quinolone compounds for use in treating viral infections

  摘要：

  本发明涉及喹诺酮化合物及其在治疗病毒感染中的应用。

  公开号：

  US20030069271A1

文献信息

• Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones
  作者：Maíra Bidart de Macedo、Roman Kimmel、Damijana Urankar、Martin Gazvoda、Antonio Peixoto、Freya Cools、Eveline Torfs、Luc Verschaeve、Emerson Silva Lima、Antonín Lyčka、David Milićević、Antonín Klásek、Paul Cos、Stanislav Kafka、Janez Košmrlj、Davie Cappoen

  DOI：10.1016/j.ejmech.2017.06.061

  日期：2017.9

  None of these selected derivatives showed significant acute toxicity against MRC-5 cells or early signs of genotoxicity in the Vitotox™ assay at the active concentration range. The structure activity study relation provided some insight in the further favourable substitution pattern at the 4-hydroxyquinolin-2(1H)-one scaffold and finally 6-fluoro-4-hydroxy-3-phenylquinolin-2(1H)-one (38) was selected as

  在这项研究中，设计了一个由50个成员组成的，由4-羟基喹啉2（1 H）-取代基和两个密切相关的类似物组成的文库，对该文进行了计算机模拟评分，随后进行了合成。共有13个共有3-苯基取代基的13种衍生物对10μM以下的结核分枝杆菌H37Ra和牛分枝杆菌的抑制作用最小低于15μM的AN5A对快速生长的分枝杆菌物种无活性。在活性浓度范围内，在Vitotox™分析中，这些选择的衍生物均未显示出对MRC-5细胞具有明显的急性毒性或遗传毒性的早期迹象。结构活性研究的关系为4-羟基喹啉-2（1 H）-one支架和6-氟-4-羟基-3-苯基喹啉-2（1 H）-one（1 ）的进一步有利的取代方式提供了一些见识。38）被选为库中最有前途的成员，MIC为3.2μM，针对MRC-5的CC 50为67.4μM。
• Design of Non-nucleoside Inhibitors of HIV-1 Reverse Transcriptase with Improved Drug Resistance Properties. 2.
  作者：George A. Freeman、C. Webster Andrews、Andrew L. Hopkins、Gina S. Lowell、Lee T. Schaller、Jill R. Cowan、Stephen S. Gonzales、George W. Koszalka、Richard J. Hazen、Lawrence R. Boone、Rob G. Ferris、Katrina L. Creech、Grace B. Roberts、Steven A. Short、Kurt Weaver、David J. Reynolds、John Milton、Jingshan Ren、David I. Stuart、David K. Stammers、Joseph H. Chan

  DOI：10.1021/jm040072r

  日期：2004.11.1

  HIV-1 nonnucleoside reverse transcriptase inhibitors (NNRTIs) are part of the combination therapy currently used to treat HIV infection. The features of a new NNRTI drug for HIV treatment must include selective potent activity against both wild-type virus as well as against mutant virus that have been selected by use of current antiretroviral treatment regimens. Based on analogy with known HIV-1 NNRTI inhibitors and modeling studies utilizing the X-ray crystal structure of inhibitors bound in the HIV-1 RT, a series of substituted 2-quinolones was synthesized and evaluated as HIV-1 inhibitors.
• QUINOLONE COMPOUNDS FOR USE IN TREATING VIRAL INFECTIONS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1244629A2

  公开（公告）日：2002-10-02
• [EN] QUINOLONE COMPOUNDS FOR USE IN TREATING VIRAL INFECTIONS<br/>[FR] COMPOSES DE QUINOLONE UTILISES DANS LE TRAITEMENT D'INFECTIONS VIRALES
  申请人：GLAXO GROUP LTD

  公开号：WO2001046150A2

  公开（公告）日：2001-06-28

  The present invention relates to quinolone compounds, such as compounds of formula (Ia) wherein: R1 is hydrogen; R2 is oxygen or sulfur; R3 is trifluoromethyl; cyano; C¿1-8?alkyl optionally substituted with C1-8alkyl or trifluoromethyl; or OR?15¿, wherein R15 is C¿1-8?alkyl optionally substituted with C1-8alkyl; R?4 is OR11¿, wherein R11 is C¿2-8?alkenyl optionally substituted with C1-8alkyl; C1-8alkyl optionally substituted with C1-8alkyl; C6-14arylalkyl; C3-6cycloalkyl; C3-6cycloalkylalkyl; heterocyclealkyl; heterocyclealkynyl; C3-6cycloalkylalkenyl; C6-14arylalkynyl; C3-6cycloalkylalkynyl; SR?12¿, wherein R12 is C¿3-6?cycloalkyl; S(O)R?12¿, wherein R12 is C¿3-6?cycloalkyl; or NR?13R14¿ wherein R?13 and R14¿, which may be the same or different, are hydrogen or C¿1-8?alkyl, optionally substituted with C1-8alkyl; R?5¿ is hydrogen; nitro; halogen; C¿1-8?alkyl, optionally substituted with C1-8alkyl or trifluoromethyl; R?6¿ is hydrogen; halogen; C¿1-8?alkyl; cyano: trifluoromethyl; or OR?10¿ wherein R10 is C¿1-8?alkyl or trifluoromethyl; R?7¿ is hydrogen; C¿1-8?alkyl; halogen; C6-14aryl; C1-8alkylaryl; C2-8alkynyl; heteroaryl; or OR?9¿ wherein R9 is C¿1-8?alkyl; R?8¿ is hydrogen; halogen; cyano; nitro; or OR16, wherein R16 is hydrogen or C¿1-8?alkyl optionally substituted with C1-8alkyl or trifluoromethyl; and their use in the treatment of viral infections.