N-{2-[4-(Aminosulfonyl)phenyl]ethyl}acetamide
[CAS# 41472-49-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Amide
• Name: N-{2-[4-(Aminosulfonyl)phenyl]ethyl}acetamide
• Synonyms: N-[2-(4-sulfamoylphenyl)ethyl]acetamide
• Molecular Formula: C₁₀H₁₄N₂O₃S
• Molecular Weight: 242.29
• CAS Registry Number: 41472-49-5
• EC Number: 255-386-5
• SMILES: CC(=O)NCCC1=CC=C(C=C1)S(=O)(=O)N

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.560, Calc.^*

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

Discovery and Applications

N-{2-[4-(Aminosulfonyl)phenyl]ethyl}acetamide is a chemically significant compound characterized by the presence of an acetamide group, an ethyl linkage, and a para-substituted sulfonamide phenyl group. These functional groups collectively impart unique physicochemical properties to the molecule, including its ability to engage in hydrogen bonding and hydrophilic interactions. The compound's structural complexity has made it an attractive subject for research in medicinal chemistry.

The discovery of N-{2-[4-(Aminosulfonyl)phenyl]ethyl}acetamide can be traced back to efforts to develop derivatives of sulfonamides with enhanced pharmacological activity. Sulfonamides have a long history in medicinal chemistry as they were among the first synthetic antibiotics introduced in the 1930s. The incorporation of an acetamide group into this framework was a logical extension to modulate the molecule’s biological activity, solubility, and stability.

N-{2-[4-(Aminosulfonyl)phenyl]ethyl}acetamide has been explored for various pharmaceutical applications. The aminosulfonyl group is well known for its role in inhibiting enzymatic activities, particularly carbonic anhydrases and metalloproteases. These enzymes are implicated in diseases such as glaucoma, cancer, and bacterial infections. By coupling this group with an acetamide linkage, the molecule gains enhanced metabolic stability and bioavailability, making it a promising candidate for therapeutic intervention.

The compound has demonstrated significant anti-inflammatory properties in preclinical studies. By targeting specific inflammatory mediators, it can potentially alleviate conditions such as rheumatoid arthritis and inflammatory bowel disease. Additionally, it has shown potential as a diuretic due to its ability to modulate ion transport mechanisms in renal tissues, a property attributed to the sulfonamide group’s interaction with carbonic anhydrase.

In materials science, N-{2-[4-(Aminosulfonyl)phenyl]ethyl}acetamide has been investigated for its applications in designing hydrophilic coatings and functional polymers. The presence of the sulfonamide group facilitates strong interactions with polar solvents and surfaces, making the compound suitable for use in water purification membranes or biomedical coatings.

The synthesis of this compound involves standard amide coupling reactions and the introduction of the sulfonamide group under controlled conditions. Despite its potential, challenges remain in optimizing its synthesis to achieve high yields and purity, particularly for industrial-scale production.

Future research aims to refine its pharmacokinetic properties, explore its potential synergistic effects with other drugs, and assess its environmental impact. The versatility of N-{2-[4-(Aminosulfonyl)phenyl]ethyl}acetamide highlights its importance in both medicinal and materials chemistry.

References

1993. Synthesis and pharmacological activity of 3-[(p-acetamidoalkyl) benzenesulfonyl]-thiazolidin-4-ones and thiazolines. Archives of Pharmacal Research. DOI: 10.1007/bf02974480

2007. Structural Analysis of Charge Discrimination in the Binding of Inhibitors to Human Carbonic Anhydrases I and II. Journal of the American Chemical Society. DOI: 10.1021/ja068359w

2023. TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Research. DOI: 10.1093/nar/gkad751