Pharmacophoric 2-hydroxyalkyl benzenesulfonamide: A single-step synthesis from benzenesulfonamide via hemiaminal

ortho-Acylation attempt of benzenesulfonamide afforded the corresponding hemiaminal as major product. The in situ reduction of the reaction mixture, reported herein, directly provided 2-hydroxyalkyl benzenesulfonamide, an important pharmacophoric element for designing drug-like scaffolds. Its application is demonstrated through designing a novel series of 1,5-diarylpyrazoles for cyclooxygenase-2 (COX-2) inhibition.

Graphical abstractThe hemiaminals obtained as a major product during ortho-acylation attempt of benzenesulfonamide were in situ reduced to pharmacophoric 2-hydroxyalkyl benzenesulfonamide intermediates and used in designing drug-like scaffolds.Figure optionsDownload full-size imageDownload as PowerPoint slide