Facile access to 4′-(N-acylsulfonamide) modified nucleosides and evaluation of their inhibitory activity against SARS-CoV-2 RNA cap N7-guanine-methyltransferase nsp14. Issue 38 (26th September 2022)

• Record Type: Journal Article
• Authors: Amador, Romain; Delpal, Adrien; Canard, Bruno; Vasseur, Jean-Jacques; Decroly, Etienne; Debart, Françoise; Clavé, Guillaume; Smietana, Michael
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 38(2022)
• Page Start: 7582
• Page End: 7586
• Publication Date: 2022-09-26
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01569b
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : 4′-( N -Acylsulfonamide) adenosine derivatives have been efficiently synthetized via the sulfo-click reaction and their biological activity has been evaluated as potential inhibitors of the 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 N 7-guanine-methyltransferase nsp14.