Emergence of new diseases and antimicrobial resistance, remain the driving forces behind the search for novel, biologically efficient, rapidly synthesizable, drugs. Recently, coordination compounds have gained attention because of their versatile biological properties. In this study, a new Schiff base compound named 3-Methoxy-2-(quinolin-3-ylimino)methyl phenol (MQIP) was synthesized through the condensation of o-vanillin with 3-amino quinoline. The formation of MQIP was confirmed using various analytical techniques such as 1H-NMR, 1(3)C-NMR, UV-Vis, and FT-IR spectroscopy. Theoretical studies confirmed its drug-like characteristics. Molecular docking analysis against the selected protein (8GJ9), revealed good protein-binding potential with scores ranging from -6.7 to -9.9 kcal/mol, without violating any drug-likeness rules. Experimental evaluations further established its strong antimicrobial, antioxidant, and anticancer activities. The compound showed a minimum inhibitory concentration (MIC) of 12.5 mu g/mL and inhibition zones of 20.5 mm, 20.4 mm, 21.6 mm against S. aureus, E. coli, and P. aeruginosa respectively. It also displayed antioxidant activity with an IC50 value of 139.83 +/- 0.35 mu g/mL, and anticancer potential against MCF-7 breast cancer cells with an IC50 value of 80 +/- 0.25 mu g/mL. Overall, both experimental and theoretical results indicate that MQIP is a promising drug intermediate with strong antimicrobial and anticancer properties.