260430-93-1 | 6-FLUOROQUINOLINE-2-CARBOXALDEHYDE

CAS:260430-93-1 | 6-FLUOROQUINOLINE-2-CARBOXALDEHYDE,Description

6-Fluoroquinoline-2-carbaldehyde is a chemical compound that serves as a key intermediate in the synthesis of various quinoline derivatives. These derivatives have shown significant potential in medicinal chemistry, particularly due to their antibacterial and antiplasmodial activities. The presence of the fluorine atom at the 6-position of the quinoline ring is a common feature in many bioactive compounds, which often enhances their pharmacological properties.

Synthesis Analysis

The synthesis of quinoline derivatives, including those related to 6-fluoroquinoline-2-carbaldehyde, involves several steps and can be achieved through different synthetic routes. For instance, the antibacterial agent flumequine, which is a derivative of 6-fluoroquinoline, was synthesized from 6-fluoro-2-methyl-1,2,3,4-tetrahydroquinoline (FTHQ). Another study reported the synthesis of new 6-fluoroquinoline derivatives with modifications at the 2 and 4 positions of the ring, which were tested for their antiplasmodial activity. Additionally, novel 6-fluoroquinoline-3-carboxylic acids with cyclopropane-fused substituents were synthesized for the treatment of Gram-positive infections.

Molecular Structure Analysis

The molecular structure of 6-fluoroquinoline derivatives is crucial for their biological activity. The absolute configuration of such compounds can be established through X-ray crystallography, as demonstrated in the synthesis of flumequine. The presence of specific substituents and their stereochemistry are key factors that influence the activity of these molecules against biological targets.

Chemical Reactions Analysis

6-Fluoroquinoline derivatives undergo various chemical reactions to yield compounds with potential pharmacological activities. For example, a three-component cyclization involving hydroxylamino-substituted quinoline was developed to synthesize new 6-fluoroquinolones. These reactions are essential for creating diverse chemical entities that can be screened for various biological activities.

Physical and Chemical Properties Analysis

The physical and chemical properties of 6-fluoroquinoline derivatives, such as log P, log D, and ligand efficiency, are important parameters that influence their pharmacokinetic and pharmacodynamic profiles. These properties were calculated or determined experimentally for new 6-fluoroquinoline derivatives with antiplasmodial activity. The permeability of these compounds was also assessed to predict their ability to cross biological membranes, which is crucial for their effectiveness as drugs.

Scientific Research Applications

Synthesis and Chemical Properties

• Synthesis of Quinoline Derivatives : 6-Fluoroquinoline-2-carbaldehyde is involved in the synthesis of various quinoline derivatives, which are known for their broad range of biological activities. For instance, the synthesis of 2-chloroquinoline-3-carbaldehyde and related analogs has been studied, illustrating the versatility of quinoline compounds in chemical synthesis (Hamama et al., 2018).
• Photophysical Properties : The study of quinoline derivatives also extends to their photophysical properties. For example, the synthesis and investigation of 2-hydroxyquinoline-3-carbaldehyde revealed its aggregation-induced emission enhancement (AIEE) phenomenon and optical sensing abilities, which are significant in material science (Chakraborty et al., 2018).

Biological Evaluation

• Antimicrobial Activities : Quinoline derivatives, including those synthesized from 6-Fluoroquinoline-2-carbaldehyde, have been evaluated for their antimicrobial properties. For instance, microwave-assisted synthesis of aryl aminochloro fluoroquinoline derivatives has shown moderate activity against various bacterial strains (Pirgal, 2022).
• Anti-Plasmodial Activity : Certain 6-fluoroquinoline derivatives have shown promising results in vitro and in vivo against Plasmodium falciparum, a parasite causing malaria. This highlights the potential of these compounds in antimalarial drug development (Hochegger et al., 2019).

Material Science and Sensing Applications

• Fluorescence Sensing : Some quinoline derivatives exhibit selectivity in fluorescence sensing, such as detecting specific metal ions. For example, a novel fluorescent sensor based on 8-hydroxyquinoline carbaldehyde Schiff-base showed high selectivity for Al3+ ions in weak acid aqueous conditions (Jiang et al., 2011).

Corrosion Inhibition

• Inhibition of Metal Corrosion : Quinoline derivatives, including those related to 6-fluoroquinoline-2-carbaldehyde, have been studied for their corrosion inhibition properties. They have shown excellent inhibition capabilities for mild steel in acidic solutions, indicating their potential as corrosion inhibitors in industrial applications (Lgaz et al., 2017).

Safety And Hazards

6-Fluoroquinoline-2-carbaldehyde can cause skin irritation, serious eye irritation, and may cause respiratory 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 ensuring adequate ventilation is advised.

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