ArticleChemMedChem2019
Stability and Efficiency of Mixed Aryl Phosphonate Prodrugs.
Article in ChemMedChem, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 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
15 citing papers in PubMed, 17 citations in OpenAlex.
- Cell stress activates γ9δ2 T cells via endogenous phosphoantigens and butyrophilin complex dynamics.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2026Article
- γ9δ2 T cells detect mevalonate diphosphate via BTN3A3.Cellular and molecular life sciences : CMLS · 2025Article
- Improved Synthesis of a Sub-Nanomolar Vinyl Phosphonate Inhibitor of Dehydroquinate Synthase.Molecules (Basel, Switzerland) · 2025Article
- Enhanced Plasma Stability and Potency of Aryl/Acyloxy Prodrugs of a BTN3A1 Ligand.ACS medicinal chemistry letters · 2024Article
- Diester Prodrugs of a Phosphonate Butyrophilin Ligand Display Improved Cell Potency, Plasma Stability, and Payload Internalization.Journal of medicinal chemistry · 2023Article
- The Multifaceted MEP Pathway: Towards New Therapeutic Perspectives.Molecules (Basel, Switzerland) · 2023Review
- Efficiency of bis-amidate phosphonate prodrugs.Bioorganic & medicinal chemistry letters · 2022Article
- Synthesis and Metabolism of BTN3A1 Ligands: Studies on Diene Modifications to the Phosphoantigen Scaffold.ACS medicinal chemistry letters · 2022Article
- Synthesis and Metabolism of BTN3A1 Ligands: Studies on Modifications of the Allylic Alcohol.ACS medicinal chemistry letters · 2021Article
- Aryloxy Diester Phosphonamidate Prodrugs of Phosphoantigens (ProPAgens) as Potent Activators of Vγ9/Vδ2 T-Cell Immune Responses.Journal of medicinal chemistry · 2020Article
- Potent double prodrug forms of synthetic phosphoantigens.Bioorganic & medicinal chemistry · 2020Article
- Metabolic Efficacy of Phosphate Prodrugs and the Remdesivir Paradigm.ACS pharmacology & translational science · 2020Review
- Structure-Activity Relationships of Butyrophilin 3 Ligands.ChemMedChem · 2020Review
- A luciferase lysis assay reveals in vivo malignant cell sensitization by phosphoantigen prodrugs.Biochemical pharmacology · 2019Article
- Synthesis and Bioactivity of the Alanyl Phosphonamidate Stereoisomers Derived from a Butyrophilin Ligand.ACS medicinal chemistry letters · 2019Article
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 1 country.
Funding
Abstract
A set of phosphonate prodrugs of a butyrophilin ligand was synthesized and evaluated for plasma stability and cellular activity. The mixed aryl acyloxy esters were prepared either via a standard sequence through the phosphonic acid chloride, or through the more recently reported, and more facile, triflate activation. In the best of cases, this class of prodrugs shows cellular potency similar to that of bis-acyloxyalkyl phosphonate prodrugs and plasma stability similar to that of aryl phosphonamidates. For example, {[((3E)-5-hydroxy-4-methylpent-3-en-1-yl) (naphthalen-2-yloxy)phosphoryl]oxy}methyl 2,2-dimethylpropanoate can activate BTN3A1 in K562 cells after just 15 minutes of exposure (at an EC
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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.