N-Acylsulfonamide: a valuable moiety to design new sulfa drug analogues

Abstract

Sulfonamides are the oldest class of antibiotics discovered more than 80 years ago. They are still used today despite the appearance of drug resistance phenomena that limit their prescription. Since...

Synthesis of Original Cyclic Dinucleotide Analogues Using the Sulfo-click Reaction

“…The sulfo-click reaction between a sulfonyl azide and a thioacid allows the synthesis of N -acylsulfonamide derivatives with high efficiency . We recently exploited this reaction for the preparation of 5′-bioconjugated nucleosides and for the synthesis of potential drugs acting as enzyme inhibitors . Interestingly, the N -acylsulfonamide moiety has recently appeared in an increasing number of pharmaceutical drugs for various therapeutic applications, mostly due to its ideal physicochemical properties .…”

“… , The assembly of nucleoside building blocks 3a,b and 4a,b was performed using the sulfo-click reaction under aqueous conditions to yield nucleoside dimers 5a – c (Scheme ). The reaction was complete in 10 min and provided high isolated yields (87–96%) consistent with our previous work. , The free 3′-OH of dimers 5a – c were then converted into the corresponding phosphoramidite derivatives 6a – c by reaction with 2-cyanoethyl N , N -diisopropylchlorophosphoramidite with good isolated yields (72–79%). Thereafter, the phosphoramidite function was hydrolyzed in MeCN by the addition of an aqueous Pyr.TFA salt solution.…”