Five trilobolide-steroid hybrids were synthesized using CuAAC approach. Cytotoxicity was tested on a 12 cancer and 3 non-cancerous cell lines. The most cytotoxic compounds were tested for cell-cycle analysis on CCRF-CEM line. The potency on androgen (AR) and estrogen (α,β-ER) receptors was examined. Impact on cell morphology was studied by live-cell microscopy. Compounds were tested against 8 sensitive and multiresistant bacterial and Candida strains.