New carboxamide derivatives bearing benzenesulphonamide as a selective COX-II inhibitor: Design, synthesis and structure-activity relationship

Sixteen new carboxamide derivatives bearing substituted benzenesulphonamide moiety (7a-p) were synthesized by boric acid mediated amidation of appropriate benzenesulphonamide with 2-amino-4-picoline and tested for anti-inflammatory activity. One compound 7c showed more potent anti-inflammatory activ...

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Bibliographic Details
Published in:PloS one 2017-09, Vol.12 (9), p.e0183807-e0183807
Main Authors: Ugwu, David Izuchukwu, Okoro, Uchechukwu Chris, Ahmad, Hilal
Format: Article
Language:English
Subjects:
Analgesics
Animals
Antiinflammatory agents
Bioassays
Biology and Life Sciences
Boric acid
Cancer
Carrageenan
Celecoxib
Chemical properties
Chemistry
COX-2 inhibitors
Cyclooxygenase 1 - chemistry
Cyclooxygenase 2 - chemistry
Cyclooxygenase 2 Inhibitors - chemical synthesis
Cyclooxygenase 2 Inhibitors - chemistry
Cyclooxygenase-1
Cyclooxygenase-2
Derivatives
Edema
Enzymes
HIV
Human immunodeficiency virus
Imidazoles - chemistry
Inflammation
Kinases
Male
Medicine and health sciences
Membrane Proteins - chemistry
Pharmaceuticals
Physical Sciences
Rats
Research and analysis methods
Rodents
Selectivity
Structure
Structure-Activity Relationship
Structure-activity relationships (Biochemistry)
Sulfonamides - chemistry
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Summary:Sixteen new carboxamide derivatives bearing substituted benzenesulphonamide moiety (7a-p) were synthesized by boric acid mediated amidation of appropriate benzenesulphonamide with 2-amino-4-picoline and tested for anti-inflammatory activity. One compound 7c showed more potent anti-inflammatory activity than celecoxib at 3 h in carrageenan-induced rat paw edema bioassay. Compounds 7g and 7k also showed good anti-inflammatory activity comparable to celecoxib. Compound 7c appeared selectivity index (COX-2/COX-1) better than celecoxib. Compound 7k appeared selectivity index (COX-2/COX-1) a little higher than the half of celecoxib while compound 7g is non-selective for COX-2. The LD50 of compounds 7c, 7g and 7k were comparable to celecoxib.
ISSN:1932-6203
1932-6203
DOI:10.1371/journal.pone.0183807