title: Pharmacophoric 2-hydroxyalkyl benzenesulfonamide: a single-step synthesis from benzenesulfonamide via hemiaminal.
abstract: 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.
authors.affiliation: Discovery Chemistry, Discovery Research, Dr. Reddy's Laboratories Ltd., Bollaram Road, Miyapur, Hyderabad 500 049, India. sunilkumarsingh@drreddys.com
authors.forename: Sunil K
authors.initials: SK
authors.lastname: Singh
authors.forename: S
authors.initials: S
authors.lastname: Shivaramakrishna
authors.forename: V
authors.initials: V
authors.lastname: Saibaba
authors.forename: K Srinivas
authors.initials: KS
authors.lastname: Rao
authors.forename: K Ravi
authors.initials: KR
authors.lastname: Ganesh
authors.forename: R
authors.initials: R
authors.lastname: Vasudev
authors.forename: P Praveen
authors.initials: PP
authors.lastname: Kumar
authors.forename: J Moses
authors.initials: JM
authors.lastname: Babu
authors.forename: K
authors.initials: K
authors.lastname: Vyas
authors.forename: Y Koteswar
authors.initials: YK
authors.lastname: Rao
authors.forename: J
authors.initials: J
authors.lastname: Iqbal
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000473:Alkanes / Q000737:chemistry*; D002257:Carbonic Anhydrase Inhibitors / Q000737:chemistry; D002626:Chemistry, Pharmaceutical; D015195:Drug Design; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013449:Sulfonamides / Q000737:chemistry*; D005680:gamma-Aminobutyric Acid; D000096926:Benzenesulfonamides
chemical_list: D000447:Aldehydes; D000473:Alkanes; D002257:Carbonic Anhydrase Inhibitors; D013449:Sulfonamides; D005680:gamma-Aminobutyric Acid; D000096926:Benzenesulfonamides