Abstract <p><b>Objective:</b> The design of three small groups of ursane acylthioureas containing terpenyl-carbamothioyl fragments and study of their anti-inflammatory and cytotoxic activity is presented. <b>Methods:</b> A series of 15 terpene acylthioureas were synthesized by condensation of three ursane primary amino derivatives holding amino groups at different distances from the triterpene skeleton with aromatic acyl isothiocyanates. The anti-inflammatory activity of the new compounds was studied in a histamine-induced inflammation model in male CD-1 mice. The cytotoxicity of hybrids was tested on tumor cells MCF7, HepG2, HeLa and hTERT-BJ1 (non-cancer control, fibroblasts). <b>Results and Discussion:</b> An anti-inflammatory effect significantly superior to that of ursolic acid was observed for a group of 28-norursane hybrids. The presence of a –CH₂– linker between the triterpene backbone and the carbamothioyl moiety significantly reduced the anti-inflammatory effect. Compounds with a – COOCH₂CH₂– linker demonstrated enhanced histamine phlogogen activity. An MTT assay on MCF7, HepG2, and HeLa tumor cells, as well as on hTERT-BJ1 cells, revealed insignificant or no cytotoxicity for all derivatives. <b>Conclusions:</b> Novel acylthioureas with terpenyl-carbamothioyl fragments are promising as synthons for heterocyclic hybrid compounds, the preparation of metal complexes, and further study of the properties and mechanisms of anti-inflammatory activity.</p>