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DESIGN, SYNTHESIS AND MOLECULAR DOCKING OF NOVEL SERINE-BASED SULPHONAMIDE BIOACTIVE COMPOUNDS AS POTENTIAL ANTIOXIDANT AND ANTIMICROBIAL AGENTS.

*Egbujor, Melford. C, Okoro, Uchechukwu. C, Okafor, Sunday, Nwankwo, N.E

Synthesis of new L-serine-based sulphonamide bioactive compounds as potential antioxidant and antimicrobial agents is reported. The reaction of p-toluenesulphonyl chloride (a) with L-serine(b) afforded 3-hydroxy-2-{[(4-methylphenyl) sulphonyl]amino}propanoic acid (c) which was acylated to afford the N-acylated compound d. Then chlorination and aminolysis of compound d gave 2-{acetyl[(4-methylphenyl) sulphonyl] amino}-3-hydroxypropanamide (e) which on nickel catalyzed amidation with aryl and heteroaryl halides afforded the various final products. The characterization of the title compounds was done with FTIR, 1H-NMR, 13C-NMR and elemental analysis. The in vitro antimicrobial and antioxidant activities were determined. The compounds were subjected to in silico evaluation and the molecular docking studied bacterial infection, fungal infections and oxidative stress. Compound d was confirmed to be the most potent antimicrobial agents while, compounds c and h displayed the best antioxidant activities. The drug-likeness investigation demonstrated that all the tested compounds were likely drugs with excellent oral bioavailability. Similarly, the molecular docking revealed that compound g (-11.19 kcal/mol) could be a more preferable antibacterial agent than penicillin (-10.89 kcal/mol) while compound c (-10.97kcal/mol) outperformed ketoconazole as an antifungal agent.The potentiality of the synthesized compounds to function as antimicrobial and antioxidant agents was confirmed. Keywords: Serine; carboxamide; sulphonamide; antimicrobial activity; antioxidant activity; molecular docking.

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