3-acetyl-7-fluoro-4(1H)-quinolinone | 1023293-76-6

• 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: 3-acetyl-7-fluoro-4(1H)-quinolinone
• 英文别名: 3-acetyl-7-fluoroquinolin-4(1H)-one；3-Acetyl-7-fluoroquinolin-4(1H)-one；3-acetyl-7-fluoro-1H-quinolin-4-one
• CAS: 1023293-76-6
• 化学式: C₁₁H₈FNO₂
• 分子量: 205.188
• InChiKey: CQNHDIDITISZSJ-UHFFFAOYSA-N

物化性质

• 熔点：
  270-271 °C(Solv: isopropanol (67-63-0))
• 沸点：
  346.1±42.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetyl-7-fluoro-4(1H)-quinolinone 在 potassium carbonate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 3-acetyl-1-[(4-fluorophenyl)methyl]-7-(piperazin-1-yl)quinolin-4(1H)-one
  参考文献：
  名称：

  Basic Quinolinonyl Diketo Acid Derivatives as Inhibitors of HIV Integrase and their Activity against RNase H Function of Reverse Transcriptase

  摘要：

  A series of antiviral basic quinolinonyl diketo acid derivatives were developed as inhibitors of HIV-1 IN. Compounds 12d,f,i inhibited HIV-1 IN with IC50 values below 100 nM for strand transfer and showed a 2 order of magnitude selectivity over 3'-processing. These strand transfer selective inhibitors also inhibited HIV-1 RNase H with low micromolar potencies. Molecular modeling studies based on both the HIV-1 IN and RNase H catalytic core domains provided new structural insights for the future development of these compounds as dual HIV-1 IN and RNase H inhibitors.

  DOI：

  10.1021/jm5001503
• 作为产物：
  描述：

  3-氟苯胺 、 乙酰乙酸乙酯 、 原甲酸三乙酯 在 diphenyl ether-biphenyl eutectic 作用下， 反应 8.0h， 以41%的产率得到3-acetyl-7-fluoro-4(1H)-quinolinone
  参考文献：
  名称：

  Basic Quinolinonyl Diketo Acid Derivatives as Inhibitors of HIV Integrase and their Activity against RNase H Function of Reverse Transcriptase

  摘要：

  A series of antiviral basic quinolinonyl diketo acid derivatives were developed as inhibitors of HIV-1 IN. Compounds 12d,f,i inhibited HIV-1 IN with IC50 values below 100 nM for strand transfer and showed a 2 order of magnitude selectivity over 3'-processing. These strand transfer selective inhibitors also inhibited HIV-1 RNase H with low micromolar potencies. Molecular modeling studies based on both the HIV-1 IN and RNase H catalytic core domains provided new structural insights for the future development of these compounds as dual HIV-1 IN and RNase H inhibitors.

  DOI：

  10.1021/jm5001503

文献信息

• Novel Quinolinonyl Diketo Acid Derivatives as HIV-1 Integrase Inhibitors: Design, Synthesis, and Biological Activities
  作者：Roberto Di Santo、Roberta Costi、Alessandra Roux、Gaetano Miele、Giuliana Cuzzucoli Crucitti、Alberto Iacovo、Federica Rosi、Antonio Lavecchia、Luciana Marinelli、Carmen Di Giovanni、Ettore Novellino、Lucia Palmisano、Mauro Andreotti、Roberta Amici、Clementina Maria Galluzzo、Lucia Nencioni、Anna Teresa Palamara、Yves Pommier、Christophe Marchand

  DOI：10.1021/jm8001422

  日期：2008.8.1

  Novel quinolinonyl diketo acids were designed to obtain integrase (IN) inhibitors selectively active against the strand transfer (ST) step of the HIV integration process. Those new compounds are characterized by a single aryl diketo acid (DKA) chain in comparison to 4, a bifunctional diketo acid reported by our group as an anti-IN agent highly potent against both the 3'-processing and ST steps. Compound 6d was the most potent derivative in IN enzyme assays, while 6i showed the highest potency against HIV-1 in acutely infected cells. The selective inhibition of ST suggested the newly designed monofunctional DKAs bind the IN-DNA acceptor site without affecting the DNA donor site.
• Basic Quinolinonyl Diketo Acid Derivatives as Inhibitors of HIV Integrase and their Activity against RNase H Function of Reverse Transcriptase
  作者：Roberta Costi、Mathieu Métifiot、Suhman Chung、Giuliana Cuzzucoli Crucitti、Kasthuraiah Maddali、Luca Pescatori、Antonella Messore、Valentina Noemi Madia、Giovanni Pupo、Luigi Scipione、Silvano Tortorella、Francesco Saverio Di Leva、Sandro Cosconati、Luciana Marinelli、Ettore Novellino、Stuart F. J. Le Grice、Angela Corona、Yves Pommier、Christophe Marchand、Roberto Di Santo

  DOI：10.1021/jm5001503

  日期：2014.4.24

  A series of antiviral basic quinolinonyl diketo acid derivatives were developed as inhibitors of HIV-1 IN. Compounds 12d,f,i inhibited HIV-1 IN with IC50 values below 100 nM for strand transfer and showed a 2 order of magnitude selectivity over 3'-processing. These strand transfer selective inhibitors also inhibited HIV-1 RNase H with low micromolar potencies. Molecular modeling studies based on both the HIV-1 IN and RNase H catalytic core domains provided new structural insights for the future development of these compounds as dual HIV-1 IN and RNase H inhibitors.