16499-62-0 | 4-chloro-7-fluoro-quinazoline

CAS:16499-62-0 | 4-chloro-7-fluoro-quinazoline,Description

4-Chloro-7-fluoroquinazoline is a compound that is structurally related to various quinoline derivatives, which have been extensively studied for their potential pharmacological properties. Quinoline derivatives are known for their complex formation with ferriprotoporphyrin IX, inhibition of beta-hematin formation, and antiplasmodial activity, which are crucial in the treatment of malaria. Additionally, these compounds have been explored for their cytotoxic effects against cancer cell lines, anticonvulsant, antinociceptive, and anti-inflammatory activities, and potent antibacterial activities. The modification of the quinoline structure, such as the introduction of a fluoro group, can lead to significant changes in the biological activity and physical properties of these compounds.

Synthesis Analysis

The synthesis of 4-aminoquinoline derivatives, which are structurally related to 4-Chloro-7-fluoroquinazoline, involves the reaction of 4-chloro-7-substituted-quinolines with corresponding mono/dialkyl amines. Another related synthesis method includes the reaction of 4,7-dichloroquinoline with organylselenols, which are generated in situ, to produce 4-arylselanyl-7-chloroquinolines. Additionally, organocatalytic synthesis has been employed to create 7-chloroquinoline-1,2,3-triazoyl carboxamidesand 7-chloroquinoline-1,2,3-triazoyl-4-carboxylates. These methods demonstrate the versatility in synthesizing quinoline derivatives, which could be applied to the synthesis of 4-Chloro-7-fluoroquinazoline.

Molecular Structure Analysis

The molecular structure of quinoline derivatives is crucial for their biological activity. For instance, the presence of a 7-chloro group in the 4-aminoquinoline ring is essential for the inhibition of beta-hematin formation. The introduction of a fluoro group, as in 4-Chloro-7-fluoroquinazoline, could potentially affect the molecule's interaction with biological targets. X-ray crystallography has been used to determine the crystal structure of related compounds, providing insights into their three-dimensional conformation and potential interaction mechanisms.

Chemical Reactions Analysis

Quinoline derivatives participate in various chemical reactions that are essential for their biological activity. For example, the formation of complexes with ferriprotoporphyrin IX is a key reaction for the antiplasmodial activity of aminoquinolines. The reactivity of the quinoline nucleus can also be modified by substituents, which can lead to the synthesis of compounds with different pharmacological properties.

Physical and Chemical Properties Analysis

The physical and chemical properties of quinoline derivatives, such as solubility, melting point, and stability, are influenced by the substituents on the quinoline nucleus. For example, the introduction of a fluoro group can affect the lipophilicity and, consequently, the absorption and distribution of the compound within the body. The photophysical properties, such as absorption and emission spectra, are also important for the potential use of these compounds as fluorescent probes or in photodynamic therapy.

Scientific Research Applications

• Anticancer Applications : 7-Fluoroquinazoline derivatives have been identified as important intermediates in small molecule anticancer drugs. A rapid synthetic method for these compounds has been established, showing potential in anticancer drug development (Zhou et al., 2019).
• Antibacterial Properties : Research on fluoroquinolones, a major class of antibacterial agents, includes the study of 7-fluoroquinolone derivatives. These compounds have demonstrated potent antibacterial activities against both Gram-positive and Gram-negative bacteria (Kuramoto et al., 2003).
• Synthesis and Structural Studies : Studies have focused on synthesizing various halogenated 2,4-diaminoquinazolines, including 7-fluoro derivatives. These studies contribute to understanding the structural properties and potential applications of these compounds (Tomažič & Hynes, 1992) .
• Cytotoxicity Evaluation : 4-Aminoquinoline derivatives, including those with 7-fluoro substitutions, have been synthesized and examined for cytotoxic effects on human breast tumor cell lines. This research contributes to the development of new classes of anticancer agents (Zhang et al., 2007).
• Antioxidative and Prooxidative Effects : Studies have explored the antioxidative and prooxidative effects of 4-hydroxyquinoline derivatives, including 7-fluoro-4-hydroxyquinoline. These findings have implications for the development of antioxidant drugs (Liu et al., 2002).
• Anticancer Properties of Indole-Aminoquinazoline Hybrids : Indole-aminoquinazolines, prepared from 2-aryl-4-chloroquinazolines, have shown significant cytotoxicity against various cancer cell lines. These compounds demonstrate potential as anticancer agents (Mphahlele et al., 2018).
• Insomnia Treatment : Research on dual orexin receptor antagonists for treating insomnia has included the development of compounds with chloro and fluoroquinazoline rings. This research contributes to novel therapeutic approaches for insomnia (Cox et al., 2010).
• Acetylcholinesterase Inhibitors and Memory Improvement : Some 4-arylselanyl-7-chloroquinolines, synthesized as potential acetylcholinesterase inhibitors, have shown promising results in improving memory in animal models. This research is relevant for treating Alzheimer's disease and other neurodegenerative disorders (Duarte et al., 2017).

Safety And Hazards

The safety information for 4-Chloro-7-fluoroquinazoline includes several hazard statements: H302 (Harmful if swallowed), H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation). Precautionary measures include avoiding breathing dust, gas, or vapors, and avoiding contact with skin and eyes.

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