Production Method 1

260430-93-1

86324-51-8

Reaction Conditions

1.1 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium chlorite Solvents: tert-Butanol ,  2-Methyl-2-butene ,  Water ;  5 min, rt; overnight, rt

Reference

Synthesis and Characterization of Iron(II) Quinaldate Complexes

Houghton, Dylan T.; et al, Inorganic Chemistry, 2010, 49(3), 879-887

Production Method 2

1128-61-6

86324-51-8

Reaction Conditions

1.1 Reagents: Selenium dioxide Solvents: 1,4-Dioxane ;  2 h, reflux

Reference

Synthesis and characterization of 3-hydroxy-4,5-dihydro[1,2,3]oxadiazolo[3,4-A]quinolin-10-ium and its fluoro derivative

Chandrasekhar, Roshini; et al, International Journal of ChemTech Research, 2011, 3(3), 1125-1128

Production Method 3

1128-61-6

86324-51-8

Reaction Conditions

1.1 Reagents: Selenium dioxide Solvents: 1,4-Dioxane ;  3 h, 80 °C
1.2 Reagents: 2-Methyl-2-butene ,  Monosodium phosphate ,  Sodium chlorite Solvents: tert-Butanol ,  Water ;  4 h, 25 °C

Reference

3-Thio-1,2,4-triazoles, novel somatostatin sst2/sst5 agonists

Contour-Galcera, Marie-Odile; et al, Bioorganic & Medicinal Chemistry Letters, 2005, 15(15), 3555-3559

Production Method 4

86324-51-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Toluene ,  Water ;  100 °C; 3 h, 100 °C; 100 °C → rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  neutralized, rt
2.1 Reagents: Selenium dioxide Solvents: 1,4-Dioxane ;  2 h, reflux

Reference

Synthesis and characterization of 3-hydroxy-4,5-dihydro[1,2,3]oxadiazolo[3,4-A]quinolin-10-ium and its fluoro derivative

Chandrasekhar, Roshini; et al, International Journal of ChemTech Research, 2011, 3(3), 1125-1128

6-Fluoroquinoline-2-carboxylic acid Raw materials

• 6-Fluoro-2-methylquinoline
• 6-Fluoroquinoline-2-carbaldehyde

6-Fluoroquinoline-2-carboxylic acid Preparation Products

• 6-Fluoroquinoline-2-carboxylic acid (86324-51-8)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Quinolines and derivatives Quinoline carboxylic acids

Introduction to 6-Fluoroquinoline-2-carboxylic acid (CAS No. 86324-51-8)

6-Fluoroquinoline-2-carboxylic acid, identified by its Chemical Abstracts Service (CAS) number 86324-51-8, is a fluorinated quinoline derivative that has garnered significant attention in the field of pharmaceutical chemistry and medicinal research. This compound belongs to the quinoline family, a class of heterocyclic aromatic compounds known for their broad spectrum of biological activities. The introduction of a fluorine atom at the 6-position of the quinoline ring enhances its pharmacological properties, making it a valuable scaffold for the development of novel therapeutic agents.

The structural features of 6-Fluoroquinoline-2-carboxylic acid contribute to its unique chemical and biological properties. The fluorine atom, being highly electronegative, influences the electronic distribution within the molecule, thereby affecting its reactivity and binding affinity to biological targets. This modification has been strategically employed to improve metabolic stability, enhance binding interactions with enzymes and receptors, and modulate pharmacokinetic profiles. Such attributes make this compound a promising candidate for further exploration in drug discovery.

In recent years, there has been a surge in research focused on developing novel antimicrobial agents due to the increasing prevalence of drug-resistant pathogens. Quinoline derivatives have long been recognized for their antimicrobial properties, and the introduction of fluorine has further augmented their efficacy. Studies have demonstrated that fluorinated quinolines exhibit enhanced activity against Gram-negative bacteria, including those that are resistant to conventional fluoroquinolones. This has opened up new avenues for the development of next-generation antibiotics.

The carboxylic acid moiety at the 2-position of the quinoline ring provides a site for further functionalization, allowing chemists to tailor the molecule's properties for specific applications. For instance, this group can be used to form esters or amides, which can then be incorporated into more complex drug molecules. Such modifications are crucial for optimizing pharmacokinetic parameters such as solubility, bioavailability, and tissue distribution.

Recent advancements in computational chemistry and molecular modeling have facilitated the rapid design and optimization of fluorinated quinoline derivatives like 6-Fluoroquinoline-2-carboxylic acid. These techniques enable researchers to predict the binding affinity of the compound to target proteins with high accuracy, thereby accelerating the drug discovery process. By leveraging these computational tools, scientists can identify potential lead compounds that exhibit favorable pharmacological profiles before proceeding to costly and time-consuming experimental validation.

The synthesis of 6-Fluoroquinoline-2-carboxylic acid involves multi-step organic reactions that require careful optimization to ensure high yield and purity. Common synthetic routes include Friedel-Crafts alkylation followed by halogenation and subsequent fluorination at the 6-position. The use of advanced catalytic systems has improved the efficiency of these reactions, making them more scalable and environmentally friendly. Additionally, green chemistry principles have been increasingly integrated into synthetic methodologies to minimize waste and reduce hazardous byproducts.

The biological activity of 6-Fluoroquinoline-2-carboxylic acid has been extensively studied in various in vitro and in vivo models. Research has shown that this compound exhibits potent inhibitory effects on certain enzymes and receptors implicated in human diseases. For example, studies have demonstrated its ability to inhibit topoisomerases, which are crucial for DNA replication and repair. By targeting these enzymes, fluorinated quinolines like this one may offer therapeutic benefits in treating cancers and infectious diseases.

The pharmacokinetic properties of 6-Fluoroquinoline-2-carboxylic acid have also been thoroughly evaluated. Preclinical studies indicate that this compound exhibits good oral bioavailability and moderate tissue penetration, suggesting its potential for systemic administration. Furthermore, its metabolic stability suggests that it may have a prolonged half-life in vivo, allowing for less frequent dosing regimens compared to existing drugs.

In conclusion, 6-Fluoroquinoline-2-carboxylic acid (CAS No. 86324-51-8) is a versatile fluorinated quinoline derivative with significant potential in pharmaceutical applications. Its unique structural features contribute to its broad spectrum of biological activities, making it a valuable scaffold for drug development. Recent advancements in synthetic methodologies and computational chemistry have further enhanced our ability to explore its therapeutic potential. As research continues to uncover new applications for this compound, it is likely to play an increasingly important role in addressing global health challenges.

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