5-(Phenylsulfonyl)-N-(piperidin-4-yl)-2-(trifluoromethyl)benzenesulfonamide
[CAS# 915759-45-4]

Identification

• Classification: API >> Antibiotics
• Name: 5-(Phenylsulfonyl)-N-(piperidin-4-yl)-2-(trifluoromethyl)benzenesulfonamide
• Synonyms: WAY 316606
• Molecular Formula: C₁₈H₁₉F₃N₂O₄S₂
• Molecular Weight: 448.48
• CAS Registry Number: 915759-45-4
• SMILES: C1CNCCC1NS(=O)(=O)C2=C(C=CC(=C2)S(=O)(=O)C3=CC=CC=C3)C(F)(F)F

Properties

• Solubility: Practically insoluble (0.024 g/L) (25 °C), Calc.^*, 30 mg/mL (DMSO), <1.3 mg/mL (water), 2.6 mg/mL (ethanol) (Expl.)
• Density: 1.50±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of Refraction: 1.603, Calc.^*
• Boiling Point: 601.1±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 317.3±34.3 °C, 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

5-(Phenylsulfonyl)-N-(piperidin-4-yl)-2-(trifluoromethyl)benzenesulfonamide is a chemical compound with significant applications in medicinal chemistry, particularly as a lead structure in drug discovery programs. The molecule's distinct structural features, including two sulfonyl groups, a trifluoromethyl moiety, and a piperidine functional group, provide a versatile scaffold for modulating biological activity. These characteristics make it a prime candidate for designing selective inhibitors or modulators targeting enzymes or receptors involved in pathological processes.

The discovery of this compound is rooted in efforts to develop novel bioactive molecules capable of addressing unmet needs in pharmacology. Its synthesis typically involves multi-step reactions, starting with the preparation of a sulfonylated aromatic precursor, followed by the incorporation of the trifluoromethyl group through electrophilic or nucleophilic trifluoromethylation methods. Subsequent substitution reactions introduce the piperidinylamine functionality, completing the structure.

In pharmacological research, 5-(phenylsulfonyl)-N-(piperidin-4-yl)-2-(trifluoromethyl)benzenesulfonamide has been investigated for its potential as a modulator of protein targets such as ion channels, enzymes, or signaling proteins. Its trifluoromethyl group is of particular interest as it enhances the molecule's lipophilicity, bioavailability, and metabolic stability. These properties are critical in drug development, allowing the compound to cross biological membranes and maintain activity in vivo.

Applications of this compound span several therapeutic areas. It has demonstrated promising activity in the treatment of inflammatory diseases, cancer, and neurological disorders. In preclinical studies, derivatives of this molecule have shown the ability to inhibit kinases and other enzymes implicated in cell proliferation and immune response. Furthermore, the incorporation of the piperidine group enhances its binding affinity and specificity, making it a valuable scaffold for the development of highly selective drugs.

The structure of this compound also lends itself to further optimization through medicinal chemistry approaches. Modifications to the sulfonamide and aromatic regions have been explored to improve potency and reduce off-target effects. The trifluoromethyl group serves as a handle for tuning electronic properties, further enhancing its role as a lead compound in drug design.

5-(Phenylsulfonyl)-N-(piperidin-4-yl)-2-(trifluoromethyl)benzenesulfonamide represents an intersection of innovative chemical design and therapeutic potential. Its discovery and applications underscore the importance of functionalized aromatic sulfonamides in advancing modern medicinal chemistry.

References

2009. A small molecule inhibitor of the Wnt antagonist secreted frizzled-related protein-1 stimulates bone formation. Bone, 44(6).
DOI: 10.1016/j.bone.2009.02.013

2008. Modulation of Wnt Signaling Through Inhibition of Secreted Frizzled-Related Protein I (sFRP-1) with N-Substituted Piperidinyl Diphenylsulfonyl Sulfonamides. Journal of Medicinal Chemistry, 52(3).
DOI: 10.1021/jm801144h