Synthesis and antiviral evaluation of acyclic azanucleosides developed from sulfanilamide as a lead structure

Abstract

The acyclic azanucleosides with 2-, 3-, or 4-aminobenzenesulfonyl function at the nitrogen atom of the sugar mimic were prepared by coupling of 2-, 3-, or 4-nitro-N-(2-pivaloyloxyethyl)-N-(pivaloyloxymethyl)benzenesulfonamide with the silylated pyrimidine nucleobases followed by the reduction of the nitro group with sodium dithionite in aqueous solution or the palladium-catalysed transfer hydrogenation. The azanucleosides were evaluated for, but found to be devoid of, activity against several RNA- and DNA-viruses in vitro.

Synthesis and Antimicrobial Activity of Novel Heterocyclic Sulfamoyl‐phenyl‐carboximidamides Derived from Clinically Applied Sulfonamides

“…Synthesis reactions of planned sulfamoyl-phenyl-carboximidamides (6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17) were carried out according to Scheme 1. This course of the synthesis was also confirmed in our previous work [27] for the reaction of methyl carbimidates with benzene-and 4-aminobenzenesulfonamide.…”

“…In fact, they exhibit diverse pharmacological activities including carbonic anhydrase inhibitors [9], diabetes [10], antifungal [11], antiviral [12], anticancer and anti-inflammatory [13], and antibacterial activities. In fact, they exhibit diverse pharmacological activities including carbonic anhydrase inhibitors [9], diabetes [10], antifungal [11], antiviral [12], anticancer and anti-inflammatory [13], and antibacterial activities.…”

Superacid mediated reactions applied to 4-aminobenzofused sultams and fluorinated 4-aminobenzene sulfonamides synthesis

“…6 Even if this method has been largely used, it requires four synthetic steps, due to the inevitable nitrogen protection and deprotection, 7 and harshness conditions (sulfonylation with concentrated sulfuric acid or oleum and chlorination with phosphorus pentachloride). Surprisingly, in spite of the recently reported very specific palladium-catalyzed transfer hydrogenation of nitrobenzene sulfonamide, 8 palladium-catalyzed intramolecular cyclization, 9 or Grignard-based sulfonamide synthesis from 4-bromoaniline, 10 no general route to 4-aminobenzene sulfonamides has been reported. As a consequence, the diversity of aminobenzene sulfonamide functionality in pharmaceutical research is limited.…”

Addition of Purines to N-Boc Imines Generated in Situ in Water: Efficient Synthesis of Novel Acyclic Purine Azanucleosides

“…Owing to their various potent pharmaceutical activities, synthesis and application of acyclic azanucleosides has attracted much attention. [4][5][6] Up to now, there are mainly two classes of acyclic azanucleosides. One class is the amino acid or peptide derivatives of pyrimidines.…”