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Eight 5‐aryl‐2‐methylquinolin‐8‐ol ligands (2–9) were prepared by a cross‐coupling Suzuki reaction from precursors brominated at position 5 (10), and positions 5 and 7 (11). These ligands were converted into new ruthenium(II)‐p‐cymene complexes (12–22) (51–94 %). The cytotoxic and antimicrobial activities of all compounds were investigated. Ligands showed higher cytotoxicity (EC50=3.1–4.8 μM) than ruthenium complexes (EC50=5.2–7.8 μM) against human melanoma cancer cells (A375). The most potent compound 7 has been shown to act via apoptosis. Some compounds were more potent as anticancer than cisplatin. Several ruthenium complexes selectively inhibited S. typhimurium and S. aureus (IC50=4.64–146.15 and 9.37–125.95 μg/mL, respectively), while most ligands were potent against C. albicans. Molecular docking studies with a protein from S. aureus suggest four key amino acids interactions, in agreement with the inhibitory potential against this bacterium.