Synthesis of N-aryl substituted p-toluenesulphonamides via nickel catalyzed amidation reaction and their antibacterial, antifungal and antioxidant activities evaluation

Abstract

In present study nickel catalyzed synthesis of N-(aryl) substituted p-toluene sulphonamides is reported. The intermediate 4-methylbenzenesulphonamide (2) was obtained by the reaction between p-toluene sulphonyl chloride and ammonium hydroxide. Various readily available aryl halides (3a-e) Substituted p-toluene sulphonamides (4a-e) were obtained by coupling 4-methylbenezenesulphonamide (2) with via Buchwald-Hartwig cross-coupling reaction. Chemical structures of synthesized compounds were confirmed using Fourier Transform Infrared (FT-1R), proton and carbon-13 Nuclear Magnetic Resonance (1H-NMR and 13C-NMR) and mass spectroscopy. The new compounds were screened for antibacterial and antifungal activities against Klebsiella pneumoniae, Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, salmonella typhi, candida albicans and Aspergillusniger using agar diffusion technique. Some of the compounds showed higher activity when compared with the standards (ciprofloxacin and ketoconazole). The sulphonamides were further screened for antioxidant activity using 1,1-diphenyl-2-picrylhydrazyl, Ferrous sulphate lipid per oxidation and Ferric reducing antioxidant power and the compound showed good antioxidant activity. Tests such as acute toxicity, liver function and kidney function was also carried out on the synthesized compounds.