N‐acylsulfonamides: Synthetic routes and biological potential in medicinal chemistry

Abstract

Sulfonamide is a common structural motif in naturally occurring and synthetic medicinal compounds. The rising interest in sulfonamides and N-acyl derivatives is attested by the large number of drugs and lead compounds identified in last years, explored in different fields of medicinal chemistry and showing biological activity. Many acylsulfonamide derivatives were designed and synthesized as isosteres of carboxylic acids, being the characteristics of these functional groups very close. Starting from chemical routes to N-acylsulfonamides, this review explores compounds of pharmaceutical interest, developed as enzymatic inhibitors or targeting receptors.

Switching the site-selectivity of C–H activation in aryl sulfonamides containing strongly coordinating N-heterocycles

“…[28][29][30][31][32][33][34][35][36][37][38] Both N-heterocycles and sulfonamides are ubiquitous in biologically active molecules owing to their hydrogen bond forming abilities and favorable drug-like properties. [39][40][41][42][43] Considering their dual pharmacological effects, switching the selectivity of the C-H functionalization of aryl sulfonamides containing strongly coordinating N-heterocycles would be invaluable in the late-stage modication of potential drug molecules ( Fig. 2A).…”

Novel Non-carboxylate Benzoylsulfonamide-Based Protein Tyrosine Phosphatase 1B Inhibitors with Non-competitive Actions

“…1 has a structure consisting of three aromatic rings, which line up via sulfonamide and amide linkers, and had modest activity and in vivo efficacy. 11,20) In the present study, we employed acylsulfonamide structure, which has been used in various enzyme inhibitors, 36) to synthesize novel compounds and to find a novel allosteric PTP1B inhibitor with good bioavailability and in vivo efficacy. The chemical structures, molecular weights, calculated log P (c log P), calculated log D 7.4 (c log D 7.4 ), and PTP1B inhibitory activities of the compounds synthesized were shown in Tables 1-3. We synthesized compound 5a, the structure of which may resemble compound IV, an allosteric inhibitor (Table 1).…”

A general strategy to develop cell permeable and fluorogenic probes for multi-colour nanoscopy

“…23 Acyl sulfonamides and acyl sulfamides are used in medicinal chemistry as anionic pharmacophores. 24,25 Amides 2-5 were prepared in three simple steps from commercially available 6-TAMRA ( Fig. 1c).…”