(1) Background: To compare the effect of selected triterpenoids with their structurally resembling derivatives, designing of the molecular ribbons was targeted to develop compounds with selectivity in their pharmacological effects. (2) Methods: In the synthetic procedures, Huisgen 1,3-dipolar cycloaddition was applied as a key synthetic step for introducing a 1,2,3-triazole ring as a part of a junction unit in the molecular ribbons. (3) Results: The antimicrobial activity, antiviral activity, and cytotoxicity of the prepared compounds were studied. Most of the molecular ribbons showed antimicrobial activity, especially on Staphylococcus aureus, Pseudomonas aeruginosa, and Enterococcus faecalis, with a 50-90% inhibition effect (c = 25 µg·mL-1). No target compound was effective against HSV-1, but 8a displayed activity against HIV-1 (EC50 = 50.6 ± 7.8 µM). Cytotoxicity was tested on several cancer cell lines, and 6d showed cytotoxicity in the malignant melanoma cancer cell line (G-361; IC50 = 20.0 ± 0.6 µM). Physicochemical characteristics of the prepared compounds were investigated, namely a formation of supramolecular gels and a self-assembly potential in general, with positive results achieved with several target compounds. (4) Conclusions: Several compounds of a series of triterpenoid molecular ribbons showed better pharmacological profiles than the parent compounds and displayed certain selectivity in their effects.

Department of Biochemistry and Microbiology University of Chemistry and Technology Prague Technická 5 16628 Prague 6 Czech Republic

Department of Chemistry of Natural Compounds University of Chemistry and Technology Prague Technická 5 16628 Prague 6 Czech Republic

Department of Experimental Biology Faculty of Science Palacký University Šlechtitelů 27 78371 Olomouc Czech Republic

Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences Flemingovo náměstí 2 16610 Prague 6 Czech Republic

Isotope Laboratory Institute of Experimental Botany of the Czech Academy of Sciences Vídeňská 1083 14220 Prague 4 Czech Republic

Ufa Institute of Chemistry of the Ufa Federal Research Centre of the Russian Academy of Sciences 71 pr Oktyabrya 450054 Ufa Russia

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Amides of moronic acid and morolic acid with the tripeptides MAG and GAM targeting antimicrobial, antiviral and cytotoxic effects

Plant Secondary Metabolites Used for the Treatment of Diseases and Drug Development