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© Research
Publication : Bioorganic Chemistry

Synthesis, antiviral and antitumor activities investigations of a series of Ribavirin C-nucleoside analogue prodrugs

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Bioorganic Chemistry - 10 Mar 2022

Sabat, N.; Ouarti, A.; Migianu-Griffoni, E.; Lecouvey, M.; Ferraris, O.; Gallier, F.; Peyrefitte, C.; Lubin-Germain, N.; Uziel, J.

Link to DOI – 10.1016/j.bioorg.2022.105723

Bioorg. Chem. 2022, 122, 105723

Phosphoramidates obtained according to the ProTide strategy are known for their ability to increase the biological activity of various nucleosides. A series of such prodrugs of SRO-91, a non-natural ribofuranosyl-1,2,3-triazole C-nucleoside obtained by a synthetic sequence involving an indium mediated alkynylation and a Huisgen cycloaddition, was prepared and the antitumor activity on 3 strains of tumor cells was investigated. Two compounds 9a and 9c exhibited interesting cell proliferative inhibitions (IC50 = 2.5–12.1 µM) on two cell lines (pancreas and lung). Moreover, concerning the antiviral activity, another phosphoramidate 14 bearing a different aryl masking group exhibited an IC50 of 5 µM on Crimean-Congo Hemorrhagic Fever orthonairovirus. In both cases, free SRO-91 presented no activity on these cell lines.