PMC:7291971 / 19527-22529 JSONTXT

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Interestingly, the dinucleoside 4 bearing an α-amino-amide specifically inhibited the viral protein Vaccinia D1-D12 complex whereas did not show any inhibition of SARS-CoV nsp14 or hRNMT. Replacing the amino acid chain by a more hydrophobic butyl or phenylpropyl chain in dinucleosides 5 and 6, respectively, we aimed at favoring the Van der Waals interactions in hydrophobic pockets of the protein. Only compound 6 showed a moderate but specific inhibition of SARS-CoV nsp14. The removal of the NH2 of the amino acid chain of the broader spectrum inhibitor 2 with an ester-ended butyl chain in compound 7 or with an acid-ended butyl chain in 8 induced weaker but more specific inhibitions of Vaccinia D1-D12 MTase and SARS-CoV nsp14. In the synthetic pathway of dinucleoside 1, the intermediate 19 bearing a 4-Ns-amide group was prepared. In view of the valuable properties of such motif in some antiviral or anticancer drugs [19,20] it seemed interesting to us to obtain dinucleoside 9 by simple acidic deprotection of 19. Of special interest, compound 9 showed a good and specific inhibition on SARS-CoV nsp14 confirming that the nosyl group contributes to the inhibitory activity with specificity. Then, we modulated the initial nosyl moiety with the nitro group in “para” position by introducing diverse hydrophobic substituents (Cl, OMe, CF3) at different positions on the phenyl ring and/or by varying the position of the nitro group in compounds 10–13. The addition of such substituents aimed at increasing the interactions with proteins. Like 9, the four dinucleosides 10–13 maintained a high inhibitory activity on SARS-CoV nsp14. The role of the nitro group on the phenyl ring was demonstrated by removing it in dinucleoside 14 bearing solely one chlorine atom in “para” position, thus the inhibitory effect was slightly decreased. These data indicated the importance of the hydrophobic Cl in “para” position. Finally, the resulting decreased inhibition when the sulfone moiety of 14 was replaced by a methylene group in compounds 15 and 16 stressed the importance of the N-arylsulfonylbenzene motif in the dinucleoside structure to maintain an effective 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