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This study introduces a series of novel Alkyl thio-1,2,4-triazole (4a-p) and mercapto-1,2,4-triazole (3a-d) compounds derived from nalidixic acid. The synthesis was streamlined, involving interactions between nalidixic acid hydrazide and various isothiocyanates to yield cyclic and alkyl(aryl) sulfide compounds, characterized using 1H NMR, 13C NMR, IR, and elemental analysis. Antioxidant capabilities were quantified through DPPH and ABTS assays, highlighting significant potential, especially for compound 3d, which demonstrated an ABTS IC50 value of 0.397 μM, on par with ascorbic acid (IC50 = 0.87 μM). Antibacterial efficacy was established through MIC assessments against a broad spectrum of Gram-positive and Gram-negative bacteria, including Candida albicans. Compounds 3b, 4e, 4h, 4j, 4i, 4m, and 4o showed broad-spectrum activity, with 4k and 4m exhibiting pronounced potency against E. coli. Molecular docking studies validated the antibacterial potential, with compounds 4f and 4h showing high binding affinities (docking scores of −9.8 and −9.6 kcal/mol, respectively), indicating robust interactions with the bacterial enzyme targets. These scores underscore the compounds' mechanistic basis for their antibacterial action and support their therapeutic promise. Furthermore, compounds 3b, 4i, and 4m, identified through drug-likeness and toxicity predictions, were highlighted for their favorable profiles, suggesting their suitability for oral antibiotic therapies. This comprehensive study, blending synthetic, in vitro, and in silico approaches, emphasizes the triazole derivatives' potential as future candidates for antibiotic and antioxidant applications, particularly spotlighting compounds 3b, 4i, and 4m due to their promising efficacy and safety profiles.

New photophysical and antioxidant materials of trimesic trihydrazide derivatives were synthesized by one-pot stage of trimesic trihydrazide and different aromatic aldehydes. All compounds were characterized by spectroscopic techniques (NMR, MS, and IR) and elemental analysis. The absorption and emission spectral characteristics of hydrazone derivatives were investigated. The absorption maxima showed red shift relative to the starting compound. While the emission maxima showed clear dependent on the type of substituents. The electron donating and electron withdrawing showed red and blue shifts relative to the starting compound, respectively. The compounds’ effectiveness as antioxidant was estimated by DPPH radical scavenging and ABTS radical cation assays in vitro which indicated that the derivatives could be used as potential antioxidants. In addition, compounds 3g, and 3i showed strong antioxidant activities according to the DPPH assay and compounds 3c and 3m exhibited good antioxidant activities in ABTS assay. Antimicrobial activity of the derivatives was estimated using a micro-broth dilution method. Furthermore, molecular geometries of all prepared derivatives were fully optimized using density functional theory (DFT) calculations at the 6-31G(d)/B3LYP level of theory.