5-Fluoro-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile
[CAS# 1887015-55-5]

Identification

• Classification: Biochemical >> Inhibitor >> Protein tyrosine kinase
• Name: 5-Fluoro-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile
• Molecular Formula: C₇H₅FN₂O
• Molecular Weight: 152.13
• CAS Registry Number: 1887015-55-5
• SMILES: CN1C(=CC=C(C1=O)F)C#N

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.535, Calc.^*
• Boiling Point: 235.5±40.0 °C (760 mmHg), Calc.^*
• Flash Point: 96.2±27.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301-P301-P302-P305-P312-P338-P351-P352

Discovery and Applications

5-Fluoro-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile is a chemical compound that belongs to the class of dihydropyridine derivatives. Dihydropyridines are widely known for their activity as calcium channel blockers, and this particular compound has attracted attention due to its potential pharmacological properties. The discovery of 5-Fluoro-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile was part of the broader research into the development of selective and potent calcium channel blockers with improved efficacy and reduced side effects. Its structure incorporates both fluorine and nitrile functional groups, which may contribute to its specific activity in various biological systems.

The development of 5-Fluoro-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile was based on the need for more targeted treatments in the management of cardiovascular conditions such as hypertension and arrhythmias. The dihydropyridine class of compounds, including nifedipine and amlodipine, is well-known for its ability to block L-type calcium channels, thereby reducing calcium influx into smooth muscle cells and cardiac muscle cells. This action leads to vasodilation and a decrease in blood pressure. The introduction of fluorine in the structure of 5-Fluoro-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile is believed to enhance its potency and improve its pharmacokinetic properties, making it a promising candidate for further development in the treatment of cardiovascular diseases.

Preclinical studies of 5-Fluoro-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile have shown that it exhibits selective calcium channel-blocking activity with a potentially favorable safety profile. The compound's effectiveness in reducing blood pressure and controlling arrhythmic events has been demonstrated in animal models, suggesting that it may offer similar therapeutic benefits to existing calcium channel blockers but with fewer side effects. The nitrile group in its structure could also impart additional chemical stability and influence its interaction with biological targets, contributing to its therapeutic potential.

In addition to its cardiovascular applications, there is growing interest in exploring 5-Fluoro-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile for other medical uses. For instance, the compound’s selective inhibition of calcium channels may offer utility in treating other diseases where abnormal calcium signaling plays a role, such as certain neurological disorders. Furthermore, the compound's unique chemical structure may be modified in future research to enhance its activity or develop novel derivatives with even greater therapeutic applications.

One of the major advantages of 5-Fluoro-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile is its potential to provide a more targeted approach to calcium channel inhibition, minimizing off-target effects seen with other calcium channel blockers. Its selective action and modified pharmacokinetics offer a promising alternative to traditional treatments for hypertension and arrhythmias. As further clinical trials and research are conducted, 5-Fluoro-1-methyl-6-oxo-1,6-dihydropyridine-2-carbonitrile may become an important part of the therapeutic landscape for cardiovascular and other diseases associated with calcium dysregulation.

References

2020. Synthesis of Olutasidenib. Synfacts. DOI: 10.1055/s-0040-1707924