A novel series of thiazolidinediones was meticulously crafted, incorporating pharmacologically relevant elements such as substituted Furfuryl/furan amine groups. These elements were intricately linked to 5' (4' sulphonylbenzylidene)]-2, 4-thiazolidinedione. The synthesis of these compounds involved a multi-step synthetic process, and their structural characterization was firmly established through comprehensive spectral analysis. To evaluate their potential, these newly synthesized compounds underwent rigorous testing for in vitro antioxidant, antibacterial activity and antifungal activity. The assessment encompassed antioxidant potential using DPPH assay, Antioxidant Assay- CUPRAC Assay, ABTS Radical Scavenging Ability, Reactive Nitrogen Oxide Scavenging Assay and Hydroxyl Free Radical Scavenging Assay. Among the synthesized compounds, Am3 and Am4 exhibited a noteworthy spectrum of antioxidant, antibacterial and antifungal activity a range of bacteria, including Gram-positive strains such as B. subtilis – MTCC 1133, as well as Gram-negative bacteria, exemplified by E. coli – MTCC452, P. aeruginosa- MTCC 3541 and fungus for instance C. albicans – MTCC 854.