A2A receptor antagonist 1 is a novel and potent antagonist of the adenosine A2A receptor and A1 receptor with Kis of 4 and 264 nM, respectively. It is chemically related to the pyrazolo[3,4-d] and pyrrolo[2,3-d] pyrimidines. Highly selective against the human A(1) receptor subtype, A2A receptor antagonist 1 was found to be effective in an in vivo Parkinson's disease model.
Physicochemical Properties
| Molecular Formula | C16H12FN5O | |
| Molecular Weight | 309.30 | |
| Exact Mass | 309.1 | |
| Elemental Analysis | C, 62.13; H, 3.91; F, 6.14; N, 22.64; O, 5.17 | |
| CAS # | 443103-97-7 | |
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| PubChem CID | 9879687 | |
| Appearance | Solid powder | |
| LogP | 2.3 | |
| Hydrogen Bond Donor Count | 1 | |
| Hydrogen Bond Acceptor Count | 6 | |
| Rotatable Bond Count | 3 | |
| Heavy Atom Count | 23 | |
| Complexity | 414 | |
| Defined Atom Stereocenter Count | 0 | |
| InChi Key | JEEJMSUHUZNTCD-UHFFFAOYSA-N | |
| InChi Code | InChI=1S/C16H12FN5O/c17-12-5-2-1-4-10(12)9-22-15-11(8-19-22)14(20-16(18)21-15)13-6-3-7-23-13/h1-8H,9H2,(H2,18,20,21) | |
| Chemical Name | 1-[(2-fluorophenyl)methyl]-4-(furan-2-yl)pyrazolo[3,4-d]pyrimidin-6-amine | |
| Synonyms | A2A receptor antagonist 1; A2A-IN-1; A2A inhibitor 1 | |
| HS Tariff Code | 2934.99.03.00 | |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | adenosine A2A Receptor ( Ki = 4 nM ); A1 Receptor ( Ki = 264 nM ) | ||
| ln Vitro | A2A receptor antagonist 1 (CPI-444 analog) is a strong adenosine A2A receptor antagonist that exhibits binding activity with Ki values of 4 and 264 nM, respectively. It is selective over the A1 receptor[1]. | ||
| ln Vivo |
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| Animal Protocol |
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| References |
[1]. Antagonists of the human adenosine A2A receptor. Part 3: Design and synthesis of pyrazolo[3,4-d]pyrimidines, pyrrolo[2,3-d]pyrimidines and 6-arylpurines. Bioorg Med Chem Lett. 2008 May 1;18(9):2924-9. |
Solubility Data
| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.08 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.08 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (8.08 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2331 mL | 16.1655 mL | 32.3311 mL | |
| 5 mM | 0.6466 mL | 3.2331 mL | 6.4662 mL | |
| 10 mM | 0.3233 mL | 1.6166 mL | 3.2331 mL |