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N-(3-Phenoxy-4-pyridinio)methanesulfonamidate
Catherine Michaux1, Caroline Charlier, Fabien Julémont
1Laboratoire de Chimie Moléculaire Structurale, Facultés Universitaires Notre-Dame de la Paix, 61 Rue de Bruxelles, B-5000 Namur, Belgium. catherine.michaux@fundp.ac.be
Acta Crystallographica. Section C, Crystal Structure Communications
|February 6, 2002
Summary
Researchers synthesized a pyridine analogue of nimesulide, a selective cyclooxygenase-2 inhibitor. Crystal analysis revealed a unique intermolecular hydrogen bond, forming infinite molecular chains.
Area of Science:
- Medicinal Chemistry
- Crystallography
- Molecular Structure
Background:
- Nimesulide is a selective cyclooxygenase-2 (COX-2) inhibitor.
- COX-2 inhibitors are important therapeutic agents.
- Understanding structural analogues can lead to novel drug development.
Purpose of the Study:
- To synthesize and characterize a strict pyridine analogue of nimesulide.
- To investigate the crystal structure and intermolecular interactions of the novel compound.
- To explore potential structure-activity relationships based on the analogue's unique features.
Main Methods:
- Chemical synthesis of the pyridine analogue (C12H12N2O3S).
- Single-crystal X-ray diffraction analysis to determine molecular and crystal structure.
- Analysis of intermolecular interactions, including hydrogen bonding.
Main Results:
- The synthesized compound is a strict pyridine analogue of nimesulide.
- Crystal structure reveals a pyridinium ring and a deprotonated sulfonamide group.
- An intermolecular charge-assisted hydrogen bond was identified, forming infinite chains along the b-axis.
Conclusions:
- The novel pyridine analogue exhibits distinct structural features compared to nimesulide.
- The observed hydrogen bonding pattern influences crystal packing and molecular arrangement.
- This structural insight could inform the design of new selective COX-2 inhibitors.