SCH 58261   

GtoPdb Ligand ID: 403

Synonyms: SCH-58261 | SCH58261
Compound class: Synthetic organic
Comment: SCH 58261 is a selective adenosine A2A receptor antagonist used as a research tool compound [9]. Reports of its effect in models of Parkinson's disease have been published [2,7].
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 100.06
Molecular weight 345.13
XLogP 3.08
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES Nc1nc2n(CCc3ccccc3)ncc2c2n1nc(n2)c1ccco1
Isomeric SMILES Nc1nc2n(CCc3ccccc3)ncc2c2n1nc(n2)c1ccco1
InChI InChI=1S/C18H15N7O/c19-18-22-16-13(11-20-24(16)9-8-12-5-2-1-3-6-12)17-21-15(23-25(17)18)14-7-4-10-26-14/h1-7,10-11H,8-9H2,(H2,19,22)
InChI Key UTLPKQYUXOEJIL-UHFFFAOYSA-N
References
1. Beukers MW, den Dulk H, van Tilburg EW, Brouwer J, Ijzerman AP. (2000)
Why are A(2B) receptors low-affinity adenosine receptors? Mutation of Asn273 to Tyr increases affinity of human A(2B) receptor for 2-(1-Hexynyl)adenosine.
Mol. Pharmacol., 58 (6): 1349-56. [PMID:11093773]
2. Chen JF, Xu K, Petzer JP, Staal R, Xu YH, Beilstein M, Sonsalla PK, Castagnoli K, Castagnoli Jr N, Schwarzschild MA. (2001)
Neuroprotection by caffeine and A(2A) adenosine receptor inactivation in a model of Parkinson's disease.
J. Neurosci., 21 (10): RC143. [PMID:11319241]
3. Dionisotti S, Ongini E, Zocchi C, Kull B, Arslan G, Fredholm BB. (1997)
Characterization of human A2A adenosine receptors with the antagonist radioligand [3H]-SCH 58261.
Br. J. Pharmacol., 121 (3): 353-60. [PMID:9179373]
4. Jacobson KA, Gao ZG. (2006)
Adenosine receptors as therapeutic targets.
Nat Rev Drug Discov, 5 (3): 247-64. [PMID:16518376]
5. Kull B, Arslan G, Nilsson C, Owman C, Lorenzen A, Schwabe U, Fredholm BB. (1999)
Differences in the order of potency for agonists but not antagonists at human and rat adenosine A2A receptors.
Biochem. Pharmacol., 57 (1): 65-75. [PMID:9920286]
6. Ongini E, Dionisotti S, Gessi S, Irenius E, Fredholm BB. (1999)
Comparison of CGS 15943, ZM 241385 and SCH 58261 as antagonists at human adenosine receptors.
Naunyn Schmiedebergs Arch. Pharmacol., 359 (1): 7-10. [PMID:9933143]
7. Simola N, Fenu S, Baraldi PG, Tabrizi MA, Morelli M. (2006)
Dopamine and adenosine receptor interaction as basis for the treatment of Parkinson's disease.
J. Neurol. Sci., 248 (1-2): 48-52. [PMID:16780890]
8. Townsend-Nicholson A, Schofield PR. (1994)
A threonine residue in the seventh transmembrane domain of the human A1 adenosine receptor mediates specific agonist binding.
J. Biol. Chem., 269 (4): 2373-6. [PMID:8300561]
9. Zocchi C, Ongini E, Conti A, Monopoli A, Negretti A, Baraldi PG, Dionisotti S. (1996)
The non-xanthine heterocyclic compound SCH 58261 is a new potent and selective A2a adenosine receptor antagonist.
J. Pharmacol. Exp. Ther., 276 (2): 398-404. [PMID:8632302]