Sulfur(vi) fluoride exchange as a key reaction for synthesizing biaryl sulfate core derivatives as potent hepatitis C virus NS5A inhibitors and their structure–activity relationship studies

Abstract

SuFEx chemistry was utilized for the design and synthesis of potent HCV NS5A inhibitors featuring a biaryl sulfate core.

Synthesis of esters and amides of 2-aryl-1-hydroxy-4-methyl-1H-imidazole-5-carboxylic acids and study of their antiviral activity against orthopoxviruses

“…Imidazole-containing molecules demonstrate a wide variety of antiviral activities. Only recently papers on antiviral activity of imidazole derivatives against Hepatitis C virus 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , Hepatitis B virus [38] , influenza A virus 39 , 40 , dengue virus 41 , 42 , Chikungunya virus [43] , rhabdoviridae 44 , 45 , 46 , 47 , 48 , herpesviridae [49] , Human Cytomegalovirus [50] , HIV-1 [51] and coronaviruses [52] have been published.…”

Sulfur(VI) Fluoride Exchange Chemistry in Solid-Phase Synthesis of Compound Arrays: Discovery of Histone Deacetylase Inhibitors

“…Thus, the present work demonstrates SuFEx chemistry as an addition to the existing arsenal of reactions for the diversification of small-molecule libraries on the solid phase. The bis-aryl sulfate diester motif itself has found limited use in medicinal chemistry previously, 78 perhaps in part due to a lack of efficient methods for its formation prior to the development of the accelerated SuFEx conditions 59 also applied herein. However, the lower number of hydrogen bond donors compared to sulfonamides, sulfamates, or sulfamides, which are accessible by SuFEx chemistry using anilines and amines, may be an attractive feature of the sulfate diesters.…”

(Hetero)Aryl Fluorosulfates (ArOSO2F): Good Coupling Partners in Transition‐metal‐catalyzed Reactions

“…Hsu's group [39] changed the fluoride leaving group as versatile covalent chemistry, developing the sulfur-triazole exchange chemistry. Fluorosulfate plays a key role in late-stage functionalization (LSF), [40][41][42] one of the most convenient routes for drug discovery in the last decade. Sharpless and coworkers [43] reported an interesting "Inverse Drug Discovery" strategy and validated covalent ligands for 11 different human proteins based on the relatively muted activity of fluorosulfate.…”