A series of novel [N-methyl-3t-alkyl-2r,6c-diarylpiperidin-4-ylidine]-5’,5’-dimethylthiazolidine-4-ones (1-4) were synthesized using recyclable and environmentally friendly Amberlite IR-120H resin as a unique and highly efficient catalyst under microwave irradiation. The synthesized compounds were characterized by FT-IR and NMR spectral studies, which indicated that the piperidine ring adopts a chair conformation with equatorial orientations of the aryl groups and the methyl group at C-3. Notably, E and Z isomers were formed for all compounds. Antibacterial, antifungal, and antimycobacterial studies revealed that all compounds exhibited good activity against the tested bacterial and fungal strains. Among these, compound 1 was particularly effective against Staphylococcus aureus compared to the standard drug Streptomycin, and it also showed higher activity against Candida albicans and Aspergillus flavus than the standard drug Amphotericin B. Furthermore, compound 1 displayed significant anti-tubercular activity against Mycobacterium tuberculosis H37Rv. These antimicrobial activities are attributed to the presence of an electron-withdrawing group in the aryl moiety, highlighting the compounds' potential for developing new antimicrobial therapies. The use of recyclable Amberlite IR-120H resin as a catalyst with microwave irradiation in the synthesis of these novel thiazolidine derivatives highlights an environmentally friendly and efficient approach.
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