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• Inflammatory disease are prevalent worldwide and can be life threatening. • The need to develop newer anti-inflammatory agents is eminent. • Carboxamides and sulphonamides are antioxidant, antimicrobial anti-inflammatory agents. • The novel compounds are good antioxidant, antimicrobial and anti-inflammatory agents. Ten new derivatives of benzenesulphonamide bearing carboxamide functionality were synthesized and investigated for their in vitro antimicrobial, antioxidant and in vivo anti-inflammatory activities. Compound 9d inhibited carrageenan induced rat-paw oedema at 93.81, 88.79 and 86.09% at 1 h, 2 h and 3 h administration respectively. In the antimicrobial activity, compound 9a (6.54, 6.69 and 6.64 mg/mL) was most potent against S. aureus , B. subtilis and C. albicans respectively, compound 9e (6.45 and 6.46 mg/mL) was most active against P. aeruginosa and A. niger respectively while compound 9i (6.24 mg/mL) was most active against E. coli. Only compound 9a (IC 50 0.3052 mg/mL) had comparable activity with Vitamin C (IC 50 0.2090 mg/mL) in the antioxidant assay. [ABSTRACT FROM AUTHOR]