5′-O-Fluorosulfonylbenzoyl Esters of Purine Nucleosides as Potential Inhibitors of NTPase/Helicase and Polymerase of<i>Flaviviridae</i>Viruses

Bretner, Maria; Schalinski, Sarah; Borowski, Peter; Kulikowski, Tadeusz

doi:10.1081/ncn-120023027

Cited by 6 publications

(4 citation statements)

References 3 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Such a mechanism could modulate the efficacy of the unwinding reaction or NTPase activity of the enzyme and therefore, affect the viral replication process. 117 – 121 Weak inhibitory effects on flaviviral NTPase/helicases were described for ribavirin triphosphate, 124 , 125 5′- O -fluorosulfonylbenzoyl esters of purine nucleosides, 126 , 127 or halogenated benzotriazole-modified nucleosides. 30 , 122 These compounds were primarily evaluated in enzyme-based assays for their putative anti-HCV activity; however, some of them have been found to inhibit also NTPase/helicases of WNV, JEV, or DENV.…”

Section: Nucleoside Inhibitors Of Flaviviral Ntpase/helicasementioning

confidence: 99%

See 1 more Smart Citation

Nucleoside analogs as a rich source of antiviral agents active against arthropod-borne flaviviruses

Eyer

Nencka

Clercq

et al. 2018

Antivir Chem Chemother

118

View full text Add to dashboard Cite

Nucleoside analogs represent the largest class of small molecule-based antivirals, which currently form the backbone of chemotherapy of chronic infections caused by HIV, hepatitis B or C viruses, and herpes viruses. High antiviral potency and favorable pharmacokinetics parameters make some nucleoside analogs suitable also for the treatment of acute infections caused by other medically important RNA and DNA viruses. This review summarizes available information on antiviral research of nucleoside analogs against arthropod-borne members of the genus Flavivirus within the family Flaviviridae, being primarily focused on description of nucleoside inhibitors of flaviviral RNA-dependent RNA polymerase, methyltransferase, and helicase/NTPase. Inhibitors of intracellular nucleoside synthesis and newly discovered nucleoside derivatives with high antiflavivirus potency, whose modes of action are currently not completely understood, have drawn attention. Moreover, this review highlights important challenges and complications in nucleoside analog development and suggests possible strategies to overcome these limitations.

show abstract

Section: Nucleoside Inhibitors Of Flaviviral Ntpase/helicasementioning

confidence: 99%

“… 30 , 122 These compounds were primarily evaluated in enzyme-based assays for their putative anti-HCV activity; however, some of them have been found to inhibit also NTPase/helicases of WNV, JEV, or DENV. 117 – 127 …”

Section: Nucleoside Inhibitors Of Flaviviral Ntpase/helicasementioning

confidence: 99%

Nucleoside analogs as a rich source of antiviral agents active against arthropod-borne flaviviruses

Eyer

Nencka

Clercq

et al. 2018

Antivir Chem Chemother

118

View full text Add to dashboard Cite

show abstract

“…Benzothiazole and pyrrolone were also potent flavivirus inactivators targeting the NS3 helicases of WNV and DENV to impede viral replication in a cell-based system [33]. In addition, the nucleoside compounds of 5 -O-fluorosulfonylbenzoyl esters of inosine (FSBI) and analogs of 1H-benzotriazole and 1H-benzimidazole were also found to be potential inhibitors against WNV, DENV or JEV in the enzyme-based assays [34][35][36]. However, the activity of most inhibitors was quite limited in the cell-based system.…”

Section: Ntpase and Helicase Inhibitorsmentioning

confidence: 99%

Mosquito-Borne Flaviviruses and Current Therapeutic Advances

Qian

2022

Viruses

View full text Add to dashboard Cite

Mosquito-borne flavivirus infections affect approximately 400 million people worldwide each year and are global threats to public health. The common diseases caused by such flaviviruses include West Nile, yellow fever, dengue, Zika infection and Japanese encephalitis, which may result in severe symptoms and disorders of multiple organs or even fatal outcomes. Till now, no specific antiviral agents are commercially available for the treatment of the diseases. Numerous strategies have been adopted to develop novel and promising inhibitors against mosquito-borne flaviviruses, including drugs targeting the critical viral components or essential host factors during infection. Research advances in antiflaviviral therapy might optimize and widen the treatment options for flavivirus infection. This review summarizes the current developmental progresses and involved molecular mechanisms of antiviral agents against mosquito-borne flaviviruses.

show abstract

“…In most cases, the COOH function was activated by transformation into the corresponding acyl chloride by reaction with SOCl 2 or (COCl) 2 with or without DMF. [32,33] Further reaction with the nucleophile provided the target amide [22,[32][33][34][35][36][37][38][39] or ester [22,33,[40][41][42][43][44][45][46] products in good to excellent yields. A similar method relied on the use of acyl fluorides; [47][48][49] however, this approach had limited application due to the lack of efficient method for their formation.…”

Section: Introductionmentioning

confidence: 99%

Chemoselective Reactions of Functionalized Sulfonyl Halides

Liashuk,

Andriashvili,

Tolmachev

et al. 2023

The Chemical Record

View full text Add to dashboard Cite

Chemoselective transformations of functionalized sulfonyl fluorides and chlorides are surveyed comprehensively. It is shown that sulfonyl fluorides provide an excellent selectivity control in their reactions. Thus, numerous conditions are tolerated by the SO2F group – from amide and ester formation to directed ortho‐lithiation and transition‐metal‐catalyzed cross‐couplings. Meanwhile, sulfur (VI) fluoride exchange (SuFEx) is also compatible with numerous functional groups, thus confirming its title of “another click reaction”. On the contrary, with a few exceptions, most transformations of functionalized sulfonyl chlorides typically occur at the SO2Cl moiety.

show abstract

5′-O-Fluorosulfonylbenzoyl Esters of Purine Nucleosides as Potential Inhibitors of NTPase/Helicase and Polymerase ofFlaviviridaeViruses

Abstract: Synthesis and interactions of guanosine, inosine and ribavirin 5'-fluorosulfonylbenzoyl esters with hepatitis C virus (HCV) and Flaviviruses NTPase/helicase and polymerase are described.

Cited by 6 publications

References 3 publications

Nucleoside analogs as a rich source of antiviral agents active against arthropod-borne flaviviruses

Nucleoside analogs as a rich source of antiviral agents active against arthropod-borne flaviviruses

Mosquito-Borne Flaviviruses and Current Therapeutic Advances

Chemoselective Reactions of Functionalized Sulfonyl Halides

Contact Info

Product

Resources

About