ArticleEuropean journal of medicinal chemistry2011
Synthesis of new 2'-deoxy-2'-fluoro-4'-azido nucleoside analogues as potent anti-HIV agents.
Article in European journal of medicinal chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
13 citing papers in PubMed.
- RNA with Azvudine Incorporated One Nucleotide Upstream of 3'-End Resists Cleavage by SARS-CoV-2 Proofreading Exonuclease.Research square · 2026Article
- Mechanism and spectrum of inhibition of viral polymerases by 2'-deoxy-2'-β-fluoro-4'-azidocytidine or azvudine.NAR molecular medicine · 2025Article
- Advances in the effectiveness and safety of azvudine treatment: a comprehensive review.Frontiers in pharmacology · 2025Review
- Drug Discovery and Exploration of Heterocycles for the Development of Anti-HIV Agents.Infectious disorders drug targets · 2025Review
- 2'-Fluorinated nucleoside chemistry for new drug discovery: achievements and prospects.National science review · 2024Review
- Bench-to-bedside: Innovation of small molecule anti-SARS-CoV-2 drugs in China.European journal of medicinal chemistry · 2023Review
- Structural basis of HIV inhibition by L-nucleosides: Opportunities for drug development and repurposing.Drug discovery today · 2022Review
- Design, Synthesis, In Silico and In Vitro Studies for New Nitric Oxide-Releasing Indomethacin Derivatives with 1,3,4-oxadiazole-2-thiol Scaffold.International journal of molecular sciences · 2021Article
- Novel Betulinic Acid-Nucleoside Hybrids with Potent Anti-HIV Activity.ACS medicinal chemistry letters · 2020Article
- Lepidiumuridine A: A New Natural Uridine Derivative as a Phytoestrogen Isolated from the Seeds ofEvidence-based complementary and alternative medicine : eCAM · 2018Article
- Versatile synthesis and biological evaluation of novel 3'-fluorinated purine nucleosides.Beilstein journal of organic chemistry · 2015Article
- Article
- Iodine monochloride facilitated deglycosylation, anomerization, and isomerization of 3-substituted thymidine analogues.Nucleosides, nucleotides & nucleic acids · 2014Article
Corrections and comments
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Authors and funding
10 authors.
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Abstract
We prepared 1-(4'-azido-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)cytosine (10) and its hydrochloride salt (11) as potential antiviral agents based on the favorable antiviral profiles of 4'-substituted nucleosides. Compounds 10 and 11 were synthesized from 1,3,5-O-tribenzoyl-2-deoxy-2-fluoro-D-arabinofuranoside in multiple steps, and their structures were unequivocally established by IR, (1)H NMR, (13)C NMR, and (19)F NMR spectroscopy, HRMS, and X-ray crystallography. Compounds 10 and 11 exhibited potent anti-HIV-1 activity (EC(50): 0.3 and 0.13 nM, respectively) without significant cytotoxicity in concentrations up to 100 μM. Compound 11 exhibited extremely potent anti-HIV activity against NL4-3 (wild-type), NL4-3 (K101E), and RTMDR viral strains, with EC(50) values of 0.086, 0.15, and 0.11 nM, respectively. Due to the high potency of 11, it was also screened against an NIH Reagent Program NRTI-resistant virus panel containing eleven mutated viral strains and for cytotoxicity against six different human cell lines. The results of this screening indicated that 11 is a novel NRTI that could be developed as an anti-AIDS clinical trial candidate to overcome drug-resistance issues.
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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.