394-68-3 | 8-FLUOROQUINOLINE

CAS:394-68-3 | 8-FLUOROQUINOLINE,Description

8-Fluoroquinoline is a fluorinated quinoline derivative that has been the subject of various studies due to its interesting chemical properties and potential applications in medicinal chemistry. It is a heterocyclic compound that has drawn significant attention for its ability to form complexes with metal ions, which can be utilized in analytical chemistry, as well as for its broad spectrum of biological activities.

Synthesis Analysis

The synthesis of 8-fluoroquinoline derivatives has been explored in several studies. For instance, a simple procedure for the synthesis of 8-fluoro-3,4-dihydroisoquinoline has been described, which is based on a directed ortho-lithiation reaction. This intermediate can then be transformed into various other compounds, such as 8-amino-tetrahydroisoquinolines and 1,2,3,4-tetrahydroisoquinoline derivatives, which are potential candidates for central nervous system drugs.

Molecular Structure Analysis

The molecular structure of 8-hydroxyquinoline derivatives has been analyzed in several studies. For example, the molecular structures of certain 8-hydroxyquinoline-substituted boron-dipyrromethene derivatives were determined by single-crystal X-ray diffraction analyses. The steric configuration and the linking group between the 8-hydroxyquinoline and the Bodipy moieties were found to affect the fluorescence properties of these compounds.

Chemical Reactions Analysis

8-Fluoroquinoline and its derivatives participate in various chemical reactions. For instance, the thioamide derivative of 8-hydroxyquinoline-benzothiazole undergoes a transformation in the presence of Hg2+ ions, resulting in a highly fluorescent amide analogue. This reaction is highly selective for Hg2+ and can be used for its detection. Another derivative exhibits selective chromogenic behavior towards Hg2+ ions, changing the color of the solution, which can be detected with the naked eye.

Physical and Chemical Properties Analysis

The physical and chemical properties of 8-fluoroquinoline derivatives have been extensively studied. For example, the phototoxicity of fluoroquinolone antibacterial agents can be reduced by introducing a methoxy group at the 8 position of the quinolone nucleus, as demonstrated in a murine model. Additionally, the ultraweak fluorescence of 8-hydroxyquinoline in water has been attributed to photoinduced ultrafast proton transfer, which is a key factor in understanding the fluorescence properties of its metal complexes.

Scientific Research Applications

• Pharmaceuticals

  • Summary of Application : Fluorinated quinolines, including 8-Fluoroquinoline, have been used as a basic structure for the search of synthetic antimalarial drugs. They have also been used in the development of drugs for the treatment of heart diseases.
  • Methods of Application : The quinoline skeleton has been used for a long time as a basic structure for the search of synthetic antimalarial drugs. The specific methods of application or experimental procedures would depend on the specific drug being developed.
  • Results or Outcomes : The introduction of a fluorine atom into azaaromatics is known to enhance the biological activity of fluorinated compounds. This has led to the development of drugs with unique properties.

• Agriculture

  • Summary of Application : A number of fluorinated quinolines have found application in agriculture.
  • Results or Outcomes : The introduction of a fluorine atom into azaaromatics is known to provide some unique properties. This has led to the development of agricultural applications with unique properties.

• Materials Science

  • Summary of Application : Fluorinated quinolines have been used as components for liquid crystals.
  • Results or Outcomes : The introduction of a fluorine atom into azaaromatics is known to provide some unique properties. This has led to the development of materials with unique properties.

• Neuroscience

  • Summary of Application : 8-Fluoroquinoline derivative 211 is capable of binding with γ-aminobutyric acid receptors, and can be used for treatment of convulsions, mental disturbances, and disorders of memory.
  • Results or Outcomes : The introduction of a fluorine atom into azaaromatics is known to enhance the biological activity of fluorinated compounds. This has led to the development of neurological applications with unique properties.

• Cyanine Dyes

  • Summary of Application : Cyanine dyes based on quinolines, including fluorinated quinolines like 8-Fluoroquinoline, make a considerable share in commercial production.
  • Results or Outcomes : The introduction of a fluorine atom into azaaromatics is known to provide some unique properties. This has led to the development of dyes with unique properties.

• Organic Light-Emitting Diodes (OLEDs)

  • Summary of Application : Fluorinated isoquinolines, including 8-Fluoroquinoline, have been used in the development of organic light-emitting diodes.
  • Results or Outcomes : The introduction of a fluorine atom into azaaromatics is known to provide some unique properties. This has led to the development of OLEDs with unique properties.

• Antibacterial Activity

  • Summary of Application : Fluorinated quinolines, including 8-Fluoroquinoline, are known to exhibit a broad spectrum of antibacterial activity.
  • Results or Outcomes : The introduction of a fluorine atom into azaaromatics is known to enhance the biological activity of fluorinated compounds. This has led to the development of antibacterial applications with unique properties.

• Enzyme Inhibitors

  • Summary of Application : Many synthetic quinolines, including 8-Fluoroquinoline, have been found to exhibit inhibitory effects on various enzymes.
  • Results or Outcomes : The introduction of a fluorine atom into azaaromatics is known to enhance the biological activity of fluorinated compounds. This has led to the development of enzyme inhibitors with unique properties.

Safety And Hazards

8-Fluoroquinoline may cause skin and eye irritation. It is recommended to avoid dust formation, breathing mist, gas or vapors, and contact with skin and eyes. Use of personal protective equipment and chemical impermeable gloves is advised.

Future Directions

Fluoroquinolones, including 8-Fluoroquinoline, are considered promising synthetic antimicrobial agents with broad-spectrum activity. They have been intensively studied for their improved pharmacokinetic properties and broad spectrum of activity. Future research may focus on further understanding their structure-activity relationship and exploring their potential applications in various fields.

More Information