Methyl 3-[[(2,6-difluorophenyl)sulfonyl]amino]-2-fluorobenzoate
[CAS# 1195768-19-4]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: Methyl 3-[[(2,6-difluorophenyl)sulfonyl]amino]-2-fluorobenzoate
• Molecular Formula: C₁₄H₁₀F₃NO₄S
• Molecular Weight: 345.29
• CAS Registry Number: 1195768-19-4
• EC Number: 812-675-6
• SMILES: COC(=O)C1=C(C(=CC=C1)NS(=O)(=O)C2=C(C=CC=C2F)F)F

Properties

• Solubility: Insoluble (2.1E^-3 g/L) (25 °C), Calc.^*
• Density: 1.507±0.06 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2014 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

Methyl 3-[[(2,6-difluorophenyl)sulfonyl]amino]-2-fluorobenzoate is a synthetic organic compound that was developed as part of efforts to create potent and selective inhibitors for various biological targets. The compound was synthesized through a series of reactions involving fluorinated aromatic compounds and sulfonylation processes, reflecting advancements in medicinal chemistry focused on integrating fluorine atoms into bioactive molecules to enhance their properties. This compound was identified through structure-activity relationship (SAR) studies aimed at optimizing the interaction between the compound and specific biological targets, potentially leading to novel therapeutic agents.

This compound is of significant interest in the development of enzyme inhibitors and receptor antagonists. The presence of fluorine atoms can enhance binding affinity, metabolic stability, and overall pharmacokinetic properties. The sulfonyl group further increases the compound's ability to form stable interactions with target proteins. These characteristics make it a promising candidate in the design of drugs for treating various diseases, including cancer, inflammatory conditions, and infectious diseases.

In oncology, compounds like methyl 3-[[(2,6-difluorophenyl)sulfonyl]amino]-2-fluorobenzoate are investigated for their potential to inhibit key enzymes involved in tumor growth and proliferation. By targeting specific enzymes or signaling pathways, these compounds can effectively slow down or halt the progression of cancer cells.

The compound's structure also lends itself to the development of anti-inflammatory drugs. By inhibiting enzymes that mediate inflammation, such as cyclooxygenase or lipoxygenase, derivatives of this compound could reduce inflammation and provide relief in conditions like rheumatoid arthritis or inflammatory bowel disease.

The structural features of methyl 3-[[(2,6-difluorophenyl)sulfonyl]amino]-2-fluorobenzoate also make it a candidate for antibacterial and antiviral drug development. The fluorinated aromatic ring can disrupt bacterial and viral protein functions, making it effective against pathogens.

Beyond pharmaceuticals, this compound has potential applications in the agrochemical industry. It can serve as a precursor to the development of new herbicides and pesticides, benefiting from the fluorine atoms' ability to enhance the activity and stability of agrochemical agents.

In materials science, the unique properties of fluorinated and sulfonylated compounds are valuable in developing advanced materials with high thermal stability and chemical resistance. These materials can be used in various high-performance applications, from coatings to electronics.

References

2014. Dabrafenib. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-04-0183