ArticleBioorganic & medicinal chemistry letters2011
Molecular probes for the A2A adenosine receptor based on a pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine scaffold.
Article in Bioorganic & medicinal chemistry letters, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
- GW-2974 and SCH-442416 modulators of tyrosine kinase and adenosine receptors can also stabilize human telomeric G-quadruplex DNA.PloS one · 2022Article
- Molecular probes for the human adenosine receptors.Purinergic signalling · 2021Review
- Chemical Probes for the Adenosine Receptors.Pharmaceuticals (Basel, Switzerland) · 2019Review
- Bitopic fluorescent antagonists of the AMedChemComm · 2017Article
- Photoaffinity Labeling of the Human AACS medicinal chemistry letters · 2017Article
- Hypothermia in mouse is caused by adenosine ANeuropharmacology · 2017Article
- Fluorescent approaches for understanding interactions of ligands with G protein coupled receptors.Biochimica et biophysica acta · 2014Review
- Synthesis of BODIPY derivatives substituted with various bioconjugatable linker groups: a construction kit for fluorescent labeling of receptor ligands.Journal of fluorescence · 2014Article
- Modulation of G protein-coupled adenosine receptors by strategically functionalized agonists and antagonists immobilized on gold nanoparticles.Purinergic signalling · 2013Article
- Fluorescent ligands for adenosine receptors.Bioorganic & medicinal chemistry letters · 2013Review
- 6-(4-Chloro-phen-yl)-2-(4-meth-oxy-phen-yl)-6,7-dihydro-4H-pyrazolo-[5,1-c][1,4]oxazine.Acta crystallographica. Section E, Structure reports online · 2011Article
- GPCR ligand dendrimer (GLiDe) conjugates: adenosine receptor interactions of a series of multivalent xanthine antagonists.Bioconjugate chemistry · 2011Article
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11 authors.
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Abstract
Pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine derivatives such as SCH 442416 display high affinity and selectivity as antagonists for the human A(2A) adenosine receptor (AR). We extended ether-linked chain substituents at the p-position of the phenyl group using optimized O-alkylation. The conjugates included an ester, carboxylic acid and amines (for amide condensation), an alkyne (for click chemistry), a fluoropropyl group (for (18)F incorporation), and fluorophore reporter groups (e.g., BODIPY conjugate 14, K(i) 15 nM). The potent and A(2A)AR-selective N-aminoethylacetamide 7 and N-[2-(2-aminoethyl)-aminoethyl]acetamide 8 congeners were coupled to polyamidoamine (PAMAM) G3.5 dendrimers, and the multivalent conjugates displayed high A(2A)AR affinity. Theoretical docking of an AlexaFluor conjugate to the receptor X-ray structure highlighted the key interactions between the heterocyclic core and the binding pocket of the A(2A)AR as well as the distal anchoring of the fluorophore. In conclusion, we have synthesized a family of high affinity functionalized congeners as pharmacological probes for studying the A(2A)AR.
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