ArticleJournal of medicinal chemistry2009
Novel 2- and 4-substituted 1H-imidazo[4,5-c]quinolin-4-amine derivatives as allosteric modulators of the A3 adenosine receptor.
Article in Journal of medicinal chemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 39 citations in OpenAlex.
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- Extrahelical Binding Site for a 1Molecular pharmacology · 2024Article
- Structure-Activity Studies of 1Journal of medicinal chemistry · 2022Article
- Characterization of Dual-Acting AACS pharmacology & translational science · 2022Article
- Update on the recent development of allosteric modulators for adenosine receptors and their therapeutic applications.Frontiers in pharmacology · 2022Review
- Adenosine Receptor Ligands: Coumarin-Chalcone Hybrids as Modulating Agents on the Activity ofMolecules (Basel, Switzerland) · 2020Article
- AMedicinal research reviews · 2018Review
- Species differences and mechanism of action of APurinergic signalling · 2018Article
- Article
- Allosteric modulation of seven transmembrane spanning receptors: theory, practice, and opportunities for central nervous system drug discovery.Journal of medicinal chemistry · 2012Article
- Protection from myocardial ischemia/reperfusion injury by a positive allosteric modulator of the A₃ adenosine receptor.The Journal of pharmacology and experimental therapeutics · 2012Article
- Functionally biased modulation of A(3) adenosine receptor agonist efficacy and potency by imidazoquinolinamine allosteric enhancers.Biochemical pharmacology · 2011Article
- International Union of Basic and Clinical Pharmacology. LXXXI. Nomenclature and classification of adenosine receptors--an update.Pharmacological reviews · 2011Review
- Allosteric modulation of purine and pyrimidine receptors.Advances in pharmacology (San Diego, Calif.) · 2011Review
Corrections and comments
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Authors and funding
5 authors at 2 institutions in 2 countries.
Funding
Abstract
4-Arylamino and 2- cycloalkyl (including amino substitution) modifications were made in a series of 1H-imidazo[4,5-c]quinolin-4-amine derivatives as allosteric modulators of the human A(3) adenosine receptor (AR). In addition to allosteric modulation of the maximum functional efficacy (in [(35)S]GTPgammaS G protein binding assay) of the A(3)AR agonist Cl-IB-MECA (15), some analogues also weakly inhibited equilibrium radioligand binding at ARs. 4-(3,5-Dichlorophenylamino) (6) or 2-(1-adamantyl) (20) substitution produced allosteric enhancement (twice the maximal agonist efficacy), with minimal inhibition of orthosteric AR binding. 2-(4-Tetrahydropyranyl) substitution abolished allosteric enhancement but preserved inhibition of orthosteric binding. Introduction of nitrogen in the six-membered ring at the 2 position, to improve aqueous solubility and provide a derivatization site, greatly reduced the allosteric enhancement. 2-(4-(Benzoylamino)cyclohexyl) analogues 23 and 24 were weak negative A(3)AR modulators. Thus, consistent with previous findings, the allosteric and orthosteric inhibitory A(3)AR effects in imidazoquinolines are structurally separable, suggesting the possible design of additional derivatives with enhanced positive or negative allosteric A(3)AR activity and improved selectivity in comparison to inhibition of orthosteric binding.
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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.