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.
Singh
Sunil K
SK
Discovery Chemistry, Discovery Research, Dr. Reddy's Laboratories Ltd., Bollaram Road, Miyapur, Hyderabad 500 049, India. sunilkumarsingh@drreddys.com
Shivaramakrishna
S
S
Saibaba
V
V
Rao
K Srinivas
KS
Ganesh
K Ravi
KR
Vasudev
R
R
Kumar
P Praveen
PP
Babu
J Moses
JM
Vyas
K
K
Rao
Y Koteswar
YK
Iqbal
J
J
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
D000447:Aldehydes; D000473:Alkanes; D002257:Carbonic Anhydrase Inhibitors; D013449:Sulfonamides; D005680:gamma-Aminobutyric Acid; D000096926:Benzenesulfonamides