ArticleBioorganic & medicinal chemistry2008
Selective A(3) adenosine receptor antagonists derived from nucleosides containing a bicyclo[3.1.0]hexane ring system.
Article in Bioorganic & medicinal chemistry, 2008. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed.
- Structure-Activity Relationship of Truncated 4'-Selenonucleosides: AACS medicinal chemistry letters · 2024Article
- Truncated (N)-Methanocarba Nucleosides as Partial Agonists at Mouse and Human AJournal of medicinal chemistry · 2020Article
- Probing structure-activity relationship in β-arrestin2 recruitment of diversely substituted adenosine derivatives.Biochemical pharmacology · 2018Article
- AMedicinal research reviews · 2018Review
- Scaffold Repurposing of Nucleosides (Adenosine Receptor Agonists): Enhanced Activity at the Human Dopamine and Norepinephrine Sodium Symporters.Journal of medicinal chemistry · 2017Article
- Extended N(6) substitution of rigid C2-arylethynyl nucleosides for exploring the role of extracellular loops in ligand recognition at the A3 adenosine receptor.Bioorganic & medicinal chemistry letters · 2014Article
- Synthesis and evaluation of N⁶-substituted apioadenosines as potential adenosine A₃ receptor modulators.Bioorganic & medicinal chemistry · 2014Article
- Synthesis and anti-renal fibrosis activity of conformationally locked truncated 2-hexynyl-N(6)-substituted-(N)-methanocarba-nucleosides as A3 adenosine receptor antagonists and partial agonists.Journal of medicinal chemistry · 2014Article
- Structural probing of off-target G protein-coupled receptor activities within a series of adenosine/adenine congeners.PloS one · 2014Article
- Methanocarba ring as a ribose modification in ligands of G protein-coupled purine and pyrimidine receptors: synthetic approaches.MedChemComm · 2013Article
- Rational design of sulfonated A3 adenosine receptor-selective nucleosides as pharmacological tools to study chronic neuropathic pain.Journal of medicinal chemistry · 2013Article
- Structural sweet spot for A1 adenosine receptor activation by truncated (N)-methanocarba nucleosides: receptor docking and potent anticonvulsant activity.Journal of medicinal chemistry · 2012Article
- Truncated Nucleosides as A(3) Adenosine Receptor Ligands: Combined 2-Arylethynyl and Bicyclohexane Substitutions.ACS medicinal chemistry letters · 2012Article
- Regio- and stereoselective synthesis of truncated 3'-aminocarbanucleosides and their binding affinity at the A3 adenosine receptor.Organic & biomolecular chemistry · 2011Article
- Truncated (N)-Methanocarba Nucleosides as A(1) Adenosine Receptor Agonists and Partial Agonists: Overcoming Lack of a Recognition Element.ACS medicinal chemistry letters · 2011Article
- Predicted structures of agonist and antagonist bound complexes of adenosine A3 receptor.Proteins · 2011Article
- Recent developments in adenosine receptor ligands and their potential as novel drugs.Biochimica et biophysica acta · 2011Review
- Pharmacophore modeling of human adenosine receptor A(₂A) antagonists.Journal of molecular modeling · 2010Article
- Synthesis and pharmacological characterization of [(125)I]MRS5127, a high affinity, selective agonist radioligand for the A3 adenosine receptor.Biochemical pharmacology · 2010Article
- 2-Dialkynyl derivatives of (N)-methanocarba nucleosides: 'Clickable' A(3) adenosine receptor-selective agonists.Bioorganic & medicinal chemistry · 2010Article
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9 authors.
Funding
Abstract
We have prepared 50-modified derivatives of adenosine and a corresponding (N)-methanocarba nucleoside series containing a bicyclo[3.1.0]hexane ring system in place of the ribose moiety. The compounds were examined in binding assays at three subtypes of adenosine receptors (ARs) and in functional assays at the A3 AR. The H-bonding ability of a group of 9-riboside derivatives containing a 50-uronamide moiety was reduced by modification of the NH; however these derivatives did not display the desired activity as selective A3 AR antagonists, as occurs with 50-N,N-dimethyluronamides. However, truncated (N)-methanocarba analogues lacking a 40-hydroxymethyl group were highly potent and selective antagonists of the human A3 AR. The compounds were synthesized from D-ribose using a reductive free radical decarboxylation of a 50-carboxy intermediate. A less efficient synthetic approach began with L-ribose, which was similar to the published synthesis of (N)-methanocarba A3AR agonists. Compounds 33b-39b (N6-3-halobenzyl and related arylalkyl derivatives) were potent A3AR antagonists with binding Ki values of 0.7-1.4 nM. In a functional assay of [35S]GTPcS binding, 33b (3-iodobenzyl) completely inhibited stimulation by NECA with a KB of 8.9 nM. Thus, a highly potent and selective series of A3AR antagonists has been described.
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