​In this study, we have successfully synthesized four symmetrical Schiff base ligands (L1, L2, L3 and L4), through the condensation reaction of 2, 2’-diamino-4, 4’-dimethyl-1, 1’-biphenyl with 2-hydroxy-3-methoxy-5-nitrobenzaldehyde, 3-bromo-5-chloro-2-hydroxybenzaldehyde, 2-hydroxy-5-methoxy-3-nitrobenzaldehyde and 3-bromo-2-hydroxy-5-nitrobenzaldehyde, respectively. Characterization of the ligands was accomplished using elemental analysis, and infrared spectroscopy. To elucidate their potential biological activity, the binding affinities of the synthesized compounds towards alpha-glucosidase inhibition were assessed employing induced-fit molecular docking calculations. The docking analysis revealed diverse interactions, such as salt-bridge, hydrogen bonding, π-stacking, and hydrophobic interactions, facilitating a proper fit of these compounds into the binding pocket of α-glucosidase. Additionally, the prepared ligands' anti-cancer potential was evaluated against various cell lines. In the initial investigation, the ICR50R of the synthesized compounds against three cancer cell lines (MDA-MB-231, MCF-7, and A549) and a normal fibroblast cell line (HDF) as a control was determined using the MTT assay. The results demonstrated a decreasing selective cytotoxic effect of compounds L1, L3, and L2 against the MDA-MB-231 breast cancer cell line. Additionally, compound L1 exhibited the lowest ICR50R value against the A549 lung cancer cell line. Subsequently, the cytotoxic impact of the bis-biphenyl salicylaldehyde Schiff base derivatives were further explored on the MDA-MB-231 breast cancer cell line using the MTT assay. The ​​