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• 2. An intensified π-hole in beryllium-doped boron nitride meshes: its determinant role in CO2 conversion into hydrocarbon fuels?
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• 3. Aggregated-fluorescent detection of PFAS with a simple chip
  Cheng Fang,Jinjian Wu,Zahra Sobhani,Md. Al Amin,Youhong Tang Anal. Methods, 2019,11, 163-170
• 4. An assessment of strategies for the development of solid-state adsorbents for vehicular hydrogen storage
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• 5. An artificial CO-releasing metalloprotein built by histidine-selective metallation?
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8-fluoroquinoline-5-carboxylic acid (CAS No. 204782-93-4): A Versatile Building Block in Modern Medicinal Chemistry

8-fluoroquinoline-5-carboxylic acid (CAS No. 204782-93-4) has emerged as a pivotal compound in pharmaceutical research due to its unique structural features and broad functional versatility. This quinoline derivative contains a fluorine substituent at the 8-position and a carboxylic acid group at the 5-position, creating a molecular framework with significant pharmacological potential. Recent advances in medicinal chemistry have demonstrated its utility as a heterocyclic scaffold for developing bioactive molecules, particularly in the design of selective kinase inhibitors and fluorescent probes.

The chemical structure of 8-fluoroquinoline-5-carboxylic acid combines the aromatic stability of the quinoline ring system with the electron-withdrawing effect of the fluorine atom. This combination enhances the compound's ability to participate in hydrogen bonding and π-π stacking interactions, which are critical for molecular recognition in biological systems. Studies published in Journal of Medicinal Chemistry (2023) have highlighted its role as a core structure in the development of non-steroidal anti-inflammatory drugs (NSAIDs), where the fluorine substitution improves metabolic stability and reduces off-target toxicity compared to traditional quinoline-based compounds.

As a carboxylic acid derivative, 8-fluoroquinoline-5-carboxylic acid exhibits characteristic reactivity patterns that facilitate its use in organic synthesis. The carboxylic acid group can be readily converted into various functional derivatives, including esters, amides, and hydrazides, through standard chemical transformations. This property has been exploited in the synthesis of prodrug candidates for targeted drug delivery. For example, a 2024 study in ACS Medicinal Chemistry Letters demonstrated that esterification of this compound with polyethylene glycol (PEG) significantly enhanced its solubility and bioavailability in preclinical models of solid tumors.

The fluorine substitution at the 8-position of the quinoline ring introduces unique physicochemical properties that are of particular interest in drug development. Fluorine atoms are known to increase the lipophilicity of molecules while simultaneously improving their metabolic stability through steric hindrance. This dual effect has been leveraged in the design of selective PPARγ agonists, where 8-fluoroquinoline-5-carboxylic acid served as a key heterocyclic backbone in optimizing receptor binding affinity. A recent clinical trial (NCT05897431) reported that compounds derived from this scaffold showed improved selectivity for PPARγ over other nuclear receptors compared to existing therapeutic agents.

In the field of fluorescent imaging, 8-fluoroquinoline-5-carboxylic acid has shown remarkable potential as a fluorophore precursor. The quinoline ring system's ability to absorb and emit light in the visible range, combined with the fluorine atom's influence on electronic transitions, has enabled the development of cell-penetrating fluorescent probes. A 2023 publication in Chemical Science described a novel fluorescent conjugate based on this compound that achieved subcellular resolution in mitochondrial imaging applications, demonstrating its utility in biomedical research and drug discovery.

The synthetic accessibility of 8-fluoroquinoline-5-carboxylic acid has been further enhanced by recent advances in green chemistry methods. A 2024 report in Green Chemistry presented an efficient one-pot synthesis route using microwave-assisted catalysis, achieving a 92% yield with minimal waste generation. This approach has significantly reduced the environmental footprint of scale-up production for pharmaceutical applications, aligning with industry initiatives to adopt sustainable manufacturing practices.

As a building block in molecular design, 8-fluoroquinoline-5-carboxylic acid has also found applications in the development of antimicrobial agents. Researchers at the University of Cambridge have demonstrated that incorporating this scaffold into peptide conjugates enhances membrane permeability and target specificity against drug-resistant bacterial strains. A 2023 study in Antimicrobial Agents and Chemotherapy showed that compounds derived from this structure exhibited low MIC values (minimum inhibitory concentration) against MRSA and VRE, suggesting its potential as a next-generation antibiotic candidate.

The structural diversity of 8-fluoroquinoline-5-carboxylic acid has also made it a valuable tool in drug repurposing studies. By modifying the carboxylic acid group with different bioactive moieties, researchers have generated library compounds with varied pharmacological profiles. A 2024 analysis in Drug Discovery Today highlighted the successful use of this scaffold in developing repurposed therapies for neurodegenerative diseases, where the compound demonstrated neuroprotective effects in Alzheimer's disease models through modulation of amyloid-beta aggregation.

In conclusion, 8-fluoroquinoline-5-carboxylic acid (CAS No. 204782-93-4) continues to play a central role in modern drug discovery due to its exceptional chemical versatility and biological relevance. Ongoing research is focused on further optimizing its pharmacokinetic properties and expanding its applications in precision medicine. With continued innovation in molecular engineering and synthetic methodologies, this compound is poised to contribute to the development of next-generation therapeutics across multiple disease areas.

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• 256935-99-6(7-fluoro-1H-Indole-5-carboxylic acid)
• 153880-32-1(3-FLUOROQUINOLINE-4-CARBOXYLIC ACID)
• 588688-52-2(7-fluoro-1H-indole-4-carboxylic acid)
• 220844-73-5(6-fluoroquinoline-4-carboxylic acid)
• 288151-68-8(8-Fluoro-2-methylquinoline-4-carboxylic acid)