Facile access to 4′-( N -acylsulfonamide) modified nucleosides and evaluation of their inhibitory activity against SARS-CoV-2 RNA cap N 7-guanine-methyltransferase nsp14 - Archive ouverte HAL Access content directly
Journal Articles Organic & Biomolecular Chemistry Year : 2022

Facile access to 4′-( N -acylsulfonamide) modified nucleosides and evaluation of their inhibitory activity against SARS-CoV-2 RNA cap N 7-guanine-methyltransferase nsp14

Abstract

N-Acylsulfonamides possess an additional carbonyl function compared to their sulfonamide analogues. Due to their unique physico-chemical properties, interest in molecules containing the N-acylsulfonamide moiety and especially nucleoside derivatives is growing in the field of medicinal chemistry. The recent renewal of interest in antiviral drugs derived from nucleosides containing a sulfonamide function has led us to evaluate the therapeutic potential of N-acylsulfonamide analogues. While these compounds are usually obtained by a difficult acylation of sulfonamides, we report here the easy and efficient synthesis of 20 4′-(N-acylsulfonamide) adenosine derivatives via the sulfo-click reaction. The target compounds were obtained from thioacid and sulfonyl azide synthons in excellent yields and were evaluated as potential inhibitors of the SARS-CoV-2 RNA cap N7-guanine-methyltransferase nsp14.
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Dates and versions

hal-03801035 , version 1 (06-10-2022)

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Romain Amador, Adrien Delpal, Bruno Canard, Jean-Jacques Vasseur, Etienne Decroly, et al.. Facile access to 4′-( N -acylsulfonamide) modified nucleosides and evaluation of their inhibitory activity against SARS-CoV-2 RNA cap N 7-guanine-methyltransferase nsp14. Organic & Biomolecular Chemistry, 2022, 20 (38), pp.7582-7586. ⟨10.1039/d2ob01569b⟩. ⟨hal-03801035⟩
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