ArticleJournal of medicinal chemistry2019
Discovery of a Series of 2'-α-Fluoro,2'-β-bromo-ribonucleosides and Their Phosphoramidate Prodrugs as Potent Pan-Genotypic Inhibitors of Hepatitis C Virus.
Article in Journal of medicinal chemistry, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
What it found
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Who cites it
14 citing papers in PubMed, 22 citations in OpenAlex.
- The 5'-Isobutyryl Ester Prodrug of 4'-Thiouridine Inhibits SARS-CoV‑2 Replication in Culture and in a Syrian Hamster Infection Model.ACS omega · 2026Article
- The 2'-α-Fluoro,2'-β-Bromo uridine phosphoramidate prodrug (2-BFU) reduces dengue virus replication and attenuates infection-induced thrombocytopenia In Vivo.Medical microbiology and immunology · 2026Article
- 1'-Cyanocytidine-5'-isobutyryl is a potent SARS-CoV-2 inhibitor in culture and infected Syrian hamsters.Science advances · 2025Article
- Mechanism of Inhibition of the Active Triphosphate Form of 2'-α-Fluoro,2'-β-bromouridine against Yellow Fever Virus RNA-Dependent RNA Polymerase.ACS infectious diseases · 2025Article
- Combating yellow fever virus with 7-deaza-7-fluoro-2'-C-methyladenosine.Antimicrobial agents and chemotherapy · 2025Article
- 6-Chlorocoumarin Conjugates with Nucleobases and Nucleosides as Potent Anti-Hepatitis C Virus Agents.Molecules (Basel, Switzerland) · 2025Article
- Synthesis of 4'-Substituted Carbocyclic Uracil Derivatives and Their Monophosphate Prodrugs as Potential Antiviral Agents.Viruses · 2023Article
- Additive-controlled asymmetric iodocyclization enables enantioselective access to both α- and β-nucleosides.Nature communications · 2023Article
- Discovery of a 2'-Fluoro,2'-Bromouridine Phosphoramidate Prodrug Exhibiting Anti-Yellow Fever Virus Activity in Culture and in Mice.Microorganisms · 2022Article
- The Inhibitory Potential of 2'-dihalo Ribonucleotides against HCV: Molecular Docking, Molecular Simulations, MM-BPSA, and DFT Studies.Molecules (Basel, Switzerland) · 2022Article
- Diastereoselective Synthesis of 2'-Dihalopyrimidine Ribonucleoside Inhibitors of Hepatitis C Virus Replication.ACS omega · 2022Article
- Anno 2021: Which antivirals for the coming decade?Annual reports in medicinal chemistry · 2021Article
- Repurposing Nucleoside Analogs for Human Coronaviruses.Antimicrobial agents and chemotherapy · 2020Article
- Synthesis and anti-HCV activity of β-d-2'-deoxy-2'-α-chloro-2'-β-fluoro and β-d-2'-deoxy-2'-α-bromo-2'-β-fluoro nucleosides and their phosphoramidate prodrugs.Bioorganic & medicinal chemistry · 2019Article
Corrections and comments
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Authors and funding
25 authors at 2 institutions in 1 country.
Funding
Abstract
Hepatitis C virus (HCV) nucleoside inhibitors display pan-genotypic activity, a high barrier to the selection of resistant virus, and are some of the most potent direct-acting agents with durable sustained virologic response in humans. Herein, we report, the discovery of β-d-2'-Br,2'-F-uridine phosphoramidate diastereomers 27 and 28, as nontoxic pan-genotypic anti-HCV agents. Extensive profiling of these two phosphorous diastereomers was performed to select one for in-depth preclinical profiling. The 5'-triphosphate formed from these phosphoramidates selectively inhibited HCV NS5B polymerase with no inhibition of human polymerases and cellular mitochondrial RNA polymerase up to 100 μM. Both are nontoxic by a variety of measures and display good stability in human blood and favorable metabolism in human intestinal microsomes and liver microsomes. Ultimately, a preliminary oral pharmacokinetics study in male beagles showed that 28 is superior to 27 and is an attractive candidate for further studies to establish its potential value as a new clinical anti-HCV agent.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.