We report here the design, synthesis, experimental and in silico evaluation of the antibacterial and antifungal activity of some new benzofquinoline derivatives. Two classes of benzofquinolinium derivatives-(benzofquinolinium salts ( ) and pyrrolobenzofquinolinium cycloadducts ( )-were designed and obtained in two steps via a direct and facile procedure: quaternization followed by a cycloaddition reaction. The synthesized compounds were characterized by elemental and spectral analysis (FT-IR, H-NMR, C-NMR). The antimicrobial assay reveals that the salts have an excellent quasi-nonselective antifungal activity against the fungus (some of them higher that the control drug nystatin) and very good antibacterial activity against the Gram positive bacterium . The compounds are inactive. Analysis of the biological data reveals interesting SAR correlations in the benzofquinolinium series of compounds. The in silico studies furnished important data concerning the pharmacodynamics, pharmacokinetics and ADMET parameters of the salts. Studies of the interaction of each salt with ATP synthase in the formed complex, reveal that salts , and have the best fit in a complex with ATP synthase. Study of the interaction of each salt with TOPO II in the formed complex reveals that salts and have the best-fit in complex with TOPO II. The in silico ADMET studies reveal that the salts have excellent drug-like properties, including a low toxicity profile. Overall, the experimental and in silico studies indicate that compounds and (from the aliphatic series), respectively, and , and (from the aromatic series), are promising leading drug candidates.