(R)-3-Fluoro-5-((3-hydroxy-7-(methylsulfonyl)-1-oxo-2,3-dihydro-1H-inden-4-YL)oxy)benzonitrile
[CAS# 2738675-96-0]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluorobenzonitrile series
• Name: (R)-3-Fluoro-5-((3-hydroxy-7-(methylsulfonyl)-1-oxo-2,3-dihydro-1H-inden-4-YL)oxy)benzonitrile
• Synonyms: 3-fluoro-5-[[(3R)-3-hydroxy-7-methylsulfonyl-1-oxo-2,3-dihydroinden-4-yl]oxy]benzonitrile
• Molecular Formula: C₁₇H₁₂FNO₅S
• Molecular Weight: 361.34
• CAS Registry Number: 2738675-96-0
• SMILES: CS(=O)(=O)C1=C2C(=O)C[C@H](C2=C(C=C1)OC3=CC(=CC(=C3)C#N)F)O

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P271-P280-P302-P304-P305-P313-P332-P337-P338-P340-P351-P352

Discovery and Applications

(R)-3-Fluoro-5-((3-hydroxy-7-(methylsulfonyl)-1-oxo-2,3-dihydro-1H-inden-4-YL)oxy)benzonitrile is a chemical compound that has gained attention due to its unique structure and potential biological activity. The compound incorporates a fluorophenyl group, a benzonitrile core, and a hydroxyl group linked to an indenyl derivative that contains a methylsulfonyl group. This structure provides the molecule with characteristics that may be advantageous in drug development, particularly for conditions where modulation of specific biological pathways is required. The presence of the fluorine atom and the methylsulfonyl group can enhance the compound's stability, solubility, and ability to interact with target proteins, making it an attractive candidate for further investigation.

The compound is a result of ongoing research aimed at discovering molecules that can interact with key receptors or enzymes involved in various diseases. The hydroxyl group and the sulfonyl group may contribute to its activity by facilitating binding to biological targets, while the fluorine atom could improve lipophilicity and membrane permeability, essential properties for compounds targeting intracellular proteins. Additionally, the indenyl component, a fused-ring structure, might contribute to increased rigidity and specificity in interactions with biological macromolecules. These features are useful in designing compounds for therapeutic use in diseases such as cancer, neurodegenerative disorders, or inflammation.

The synthesis of (R)-3-Fluoro-5-((3-hydroxy-7-(methylsulfonyl)-1-oxo-2,3-dihydro-1H-inden-4-YL)oxy)benzonitrile generally involves several key steps. The starting material, a suitable benzonitrile derivative, undergoes fluorination at the 3-position to introduce the fluorine atom. The next step involves the formation of the hydroxyl group at the 5-position, followed by the incorporation of the indenyl and methylsulfonyl moieties at the appropriate positions on the ring. Control of stereochemistry is critical to obtaining the desired (R)-enantiomer, as this can significantly influence the compound’s biological activity. The final product is isolated as a highly functionalized molecule, ready for further testing in biological assays.

In terms of applications, (R)-3-Fluoro-5-((3-hydroxy-7-(methylsulfonyl)-1-oxo-2,3-dihydro-1H-inden-4-YL)oxy)benzonitrile may show promise in drug development, particularly in the treatment of diseases where the regulation of oxidative stress, inflammation, or enzyme activity is crucial. The sulfonyl group suggests potential for interaction with proteins involved in cellular signaling, while the fluorophenyl group could aid in the compound’s ability to penetrate the blood-brain barrier, making it useful in neurological applications. The indenyl structure may allow the molecule to bind with high specificity to target proteins, reducing off-target effects and improving therapeutic efficacy.

Further studies on the compound's pharmacodynamics and pharmacokinetics are needed to evaluate its potential as a therapeutic agent. Research into its selectivity for particular enzymes or receptors, as well as its impact in preclinical models, will be key to determining its suitability for clinical development.

References

2022. Synthesis of Belzutifan. Synfacts.
DOI: 10.1055/s-0041-1738315