Synthesis, in silico guided DNA-interaction analysis, in vitro anti-oxidant evaluation, and antibacterial assay of 4-amino-5-(2-benzylidenehydrazinyl)-2H-1,2,4-triazole-3(4H)-thiones

The current research contains synthesis, DNA-interaction analysis, in vitro anti-oxidant evaluation, and antibacterial assay of triazole-azomethine hybrids. Consequently, the synthesized hybrids were subjected to molecular docking (MD), density functional theory (DFT) guided experimental DNA-interaction studies, in vitro DPPH quenching, and bactericidal assay. Subsequently, the screened hybrids displayed higher DNA binding abilities in DNA-interaction studies. Notably, the hybrids bearing 4-hydroxy-), 2-hydroxy-4-methoxy-), and 4-bromo-) groups displayed higher binding ability in the DNA grooves with respective interaction strengths in the range of 3.43–6.43 × 10–3 M−1 higher than the reference Cis-platin (3.142 × 10–3 M−1) augmented by MD and DFT analysis. Similarly, DFT-guided UV–visible spectroscopy-based anti-oxidant assay revealed potent oxidative nature of the screened hybrids. DPPH free radical scavenging ability in terms of IC50 values falls within a narrow range of 22.30–34.22 μM. The screened hybrids bearing 4-hydroxy-), 3,4-dihydroxy-), and 2,3,4-trihydroxy-) groups display highest DPPH scavenging potential with respective IC50 values of 34.22 μM, 32.11 μM, and 29.30 μM. Moreover, the synthesized hybrids were evaluated against gram-negative and positive bacterial strains, indicating their inhibitory potential as zone of inhibition (ZOI). Briefly, the screened hybrid bearing 2,3,4-trihydroxy-) group displayed ZOI (21 mm) against Pseudomonas aeruginosa (gram-negative strain) higher than Benzylpenicillin (18 mm). The remaining hybrids possess inhibitory potential comparable to the reference. Conversely, the screened hybrids showed varied responses against Staphylococcus aureus (gram-positive strain), with highest ZOI (16 mm) displayed by the hybrid with 4-hydroxy-) group. Thus, the obtained ZOI suggests the potent hybrids to be explored further as effective motifs against gram-negative and positive bacterial strains.