ArticleJournal of medicinal chemistry2006
2-triazole-substituted adenosines: a new class of selective A3 adenosine receptor agonists, partial agonists, and antagonists.
Article in Journal of medicinal chemistry, 2006. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
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Who cites it
23 citing papers in PubMed.
- Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization.Molecules (Basel, Switzerland) · 2025Article
- 2-Substituted (N)-Methanocarba AACS pharmacology & translational science · 2024Article
- Nitrogen-Centered Radicals Derived from Azidonucleosides.Molecules (Basel, Switzerland) · 2024Review
- Synthesis of Fluorescent C-C Bonded Triazole-Purine Conjugates.Journal of fluorescence · 2024Article
- 1,2,3-Triazoles as leaving groups: SBeilstein journal of organic chemistry · 2021Article
- Exploration of Alternative Scaffolds for P2YJournal of medicinal chemistry · 2020Article
- AMedicinal research reviews · 2018Review
- ADP-ribosyl-N₃: A Versatile Precursor for Divergent Syntheses of ADP-ribosylated Compounds.Molecules (Basel, Switzerland) · 2017Article
- Strain Promoted Click Chemistry of 2- or 8-Azidopurine and 5-Azidopyrimidine Nucleosides and 8-Azidoadenosine Triphosphate with Cyclooctynes. Application to Living Cell Fluorescent Imaging.Bioconjugate chemistry · 2015Article
- Azidophenyl as a click-transformable redox label of DNA suitable for electrochemical detection of DNA-protein interactions.Chemical science · 2015Article
- Synthesis and biological properties of C-2 triazolylinosine derivatives.The Journal of organic chemistry · 2012Article
- Structure-guided design of A(3) adenosine receptor-selective nucleosides: combination of 2-arylethynyl and bicyclo[3.1.0]hexane substitutions.Journal of medicinal chemistry · 2012Article
- Synthesis of purine modified 2'-C-methyl nucleosides as potential anti-HCV agents.Bioorganic & medicinal chemistry letters · 2011Article
- Azide-tetrazole equilibrium of C-6 azidopurine nucleosides and their ligation reactions with alkynes.The Journal of organic chemistry · 2010Article
- 2-Dialkynyl derivatives of (N)-methanocarba nucleosides: 'Clickable' A(3) adenosine receptor-selective agonists.Bioorganic & medicinal chemistry · 2010Article
- Functionalized congeners of A3 adenosine receptor-selective nucleosides containing a bicyclo[3.1.0]hexane ring system.Journal of medicinal chemistry · 2009Article
- Cu(I)-catalyzed Huisgen azide-alkyne 1,3-dipolar cycloaddition reaction in nucleoside, nucleotide, and oligonucleotide chemistry.Chemical reviews · 2009Review
- Medicinal chemistry of the A3 adenosine receptor: agonists, antagonists, and receptor engineering.Handbook of experimental pharmacology · 2009Review
- Inhibition of siderophore biosynthesis by 2-triazole substituted analogues of 5'-O-[N-(salicyl)sulfamoyl]adenosine: antibacterial nucleosides effective against Mycobacterium tuberculosis.Journal of medicinal chemistry · 2008Article
- Design of (N)-methanocarba adenosine 5'-uronamides as species-independent A3 receptor-selective agonists.Bioorganic & medicinal chemistry letters · 2008Article
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7 authors.
Funding
Abstract
"Click chemistry" was explored to synthesize two series of 2-(1,2,3-triazolyl)adenosine derivatives (1-14). Binding affinity at the human A(1), A(2A), and A(3)ARs (adenosine receptors) and relative efficacy at the A(3)AR were determined. Some triazol-1-yl analogues showed A(3)AR affinity in the low nanomolar range, a high ratio of A(3)/A(2A) selectivity, and a moderate-to-high A(3)/A(1) ratio. The 1,2,3-triazol-4-yl regiomers typically showed decreased A(3)AR affinity. Sterically demanding groups at the adenine C2 position tended to reduce relative A(3)AR efficacy. Thus, several 5'-OH derivatives appeared to be selective A(3)AR antagonists, i.e., 10, with 260-fold binding selectivity in comparison to the A(1)AR and displaying a characteristic docking mode in an A(3)AR model. The corresponding 5'-ethyluronamide analogues generally showed increased A(3)AR affinity and behaved as full agonists, i.e., 17, with 910-fold A(3)/A(1) selectivity. Thus, N(6)-substituted 2-(1,2,3-triazolyl)adenosine analogues constitute a novel class of highly potent and selective nucleoside-based A(3)AR antagonists, partial agonists, and agonists.
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