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Submit ReviewSCH 442416
Description: Very selective, high affinity A2A antagonist
Chemical Name: 2-(2-Furanyl)-7-[3-(4-methoxyphenyl)propyl]-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amine
Purity: ≥99% (HPLC)
Biological Activity for SCH 442416
SCH 442416 is a selective adenosine A2A receptor antagonist; binds to human and rat A2A receptors with high affinity (Ki values are 0.048 and 0.5 nM respectively). Displays > 23000-fold selectivity for hA2A over hA1 in vitro with minimal affinity for hA2B and hA3 receptors (IC50 > 10 μM). Blocks the cytoprotective effect of A2A agonist CGS-21680 (Cat.No. 1063).
Compound Libraries for SCH 442416
SCH 442416 is also offered as part of the Tocriscreen 2.0 Max. Find out more about compound libraries available from Tocris.
Technical Data for SCH 442416
| M. Wt | 389.42 |
| Formula | C20H19N7O2 |
| Storage | Store at RT |
| Purity | ≥99% (HPLC) |
| CAS Number | 316173-57-6 |
| PubChem ID | 10668061 |
| InChI Key | AEULVFLPCJOBCE-UHFFFAOYSA-N |
| Smiles | COC1=CC=C(CCCN2N=CC3=C2N=C(N)N2N=C(N=C32)C2=CC=CO2)C=C1 |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for SCH 442416
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 38.94 | 100 |
Preparing Stock Solutions for SCH 442416
The following data is based on the product molecular weight 389.42. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 2.57 mL | 12.84 mL | 25.68 mL |
| 5 mM | 0.51 mL | 2.57 mL | 5.14 mL |
| 10 mM | 0.26 mL | 1.28 mL | 2.57 mL |
| 50 mM | 0.05 mL | 0.26 mL | 0.51 mL |
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Product Datasheets for SCH 442416
References for SCH 442416
References are publications that support the biological activity of the product.
Todde et al (2000) Design, radiosynthesis, and biodistribution of a new potent and selective ligand for in vivo imaging of the adenosine A2A receptor system using positron emission tomography. J.Med.Chem. 43 4359 PMID: 11087559
Zheng et al (2007) Protective roles of adenosine A1, A2, and A3 receptors in skeletal muscle ischemia and reperfusion injury. Am.J.Physiol.Heart Circ.Physiol. 293 3685
If you know of a relevant reference for SCH 442416, please let us know.
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Keywords: SCH 442416, SCH 442416 supplier, selective, high, affinity, A2A, antagonists, Receptors, adenosines, SCH442416, adenosine, 2a, antagonist, Adenosine, 2463, Tocris Bioscience
11 Citations for SCH 442416
Citations are publications that use Tocris products. Selected citations for SCH 442416 include:
Varani et al (2011) A2A and A3 adenosine receptor expression in rheumatoid arthritis: upregulation, inverse correlation with disease activity score and suppression of inflammatory cytokine and metalloproteinase release. Arthritis Res Ther 13 R197 PMID: 22146575
Ross and Venton (2015) Adenosine transiently modulates stimulated DA release in the caudate-putamen via A1 receptors. Exp Ther Med 132 51 PMID: 25219576
Pugliese et al (2009) The adenosine A2A receptor antagonist ZM241385 enhances neuronal survival after oxygen-glucose deprivation in rat CA1 hippocampal slices. Br J Pharmacol 157 818 PMID: 19422385
Fang et al (2016) Expression of CD39 on Activated T Cells Impairs their Survival in Older Individuals. Cell Rep 14 1218 PMID: 26832412
Sassi et al (2014) Cardiac myocyte-secreted cAMP exerts paracrine action via adenosine receptor activation. J Clin Invest 124 5385 PMID: 25401477
Yu et al (2012) Effect of A(2A) receptor antagonist (SCH 442416) on the mRNA expression of glutamate aspartate transporter and glutamine synthetase in rat retinal Müller cells under hypoxic conditions in vitro. Am J Physiol Renal Physiol 3 803 PMID: 22969972
Tosolini et al (2015) Human monocyte recognition of adenosine-based cyclic dinucleotides unveils the A2a Gαs protein-coupled receptor tonic inhibition of mitochondrially induced cell death. J Neurochem 35 479 PMID: 25384972
Li et al (2014) Regulation of photoreceptor gap junction phosphorylation by adenosine in zebrafish retina. Vis Neurosci 31 237 PMID: 24844306
Núñez et al (2018) PBF509, an Adenosine A2A Receptor Antagonist With Efficacy in Rodent Models of Movement Disorders. Front Pharmacol 9 1200 PMID: 30405415
Cheng et al (2017) Structures of Human A1 and A2A Adenosine Receptors with Xanthines Reveal Determinants of Selectivity. Structure 25 1275 PMID: 28712806
Fang et al (2016) Expression of CD39 on activated T cells impairs their survival in older individuals. Cell Rep. 14 1218
Do you know of a great paper that uses SCH 442416 from Tocris? Please let us know.
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