The synthesis and pharmacological activity of N-substituted derivatives of 1,8,11,11-tetramethyl-4-azatricyclo[5.2.2.0(2,6)]undec-8-ene-3,5-dione (1) are described. The molecular structure of starting compound (1) was confirmed by elemental analysis, 13C NMR and X-ray crystallography. The structures of derivatives were confirmed by 1H NMR and mass spectra. The compounds were investigated for antibacterial activity, including Gram-positive cocci, Gram-negative rods, and antifungal activity. Studied compounds were evaluated also for their cytotoxicity and anti-HIV-1 activity in MT-4 cells.