CGS 21680   Click here for help

GtoPdb Ligand ID: 375

Synonyms: CGS-21680 | CGS21680
PDB Ligand
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 12
Hydrogen bond donors 6
Rotatable bonds 11
Topological polar surface area 197.74
Molecular weight 499.22
XLogP 1.22
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCNC(=O)C1OC(C(C1O)O)n1cnc2c1nc(NCCc1ccc(cc1)CCC(=O)O)nc2N
Isomeric SMILES CCNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(NCCc1ccc(cc1)CCC(=O)O)nc2N
InChI InChI=1S/C23H29N7O6/c1-2-25-21(35)18-16(33)17(34)22(36-18)30-11-27-15-19(24)28-23(29-20(15)30)26-10-9-13-5-3-12(4-6-13)7-8-14(31)32/h3-6,11,16-18,22,33-34H,2,7-10H2,1H3,(H,25,35)(H,31,32)(H3,24,26,28,29)/t16-,17+,18-,22+/m0/s1
InChI Key PAOANWZGLPPROA-RQXXJAGISA-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. Bosch MP, Campos F, Niubó I, Rosell G, Díaz JL, Brea J, Loza MI, Guerrero A. (2004)
Synthesis and biological activity of new potential agonists for the human adenosine A2A receptor.
J. Med. Chem., 47 (16): 4041-53. [PMID:15267242]
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. Gao ZG, Mamedova LK, Chen P, Jacobson KA. (2004)
2-Substituted adenosine derivatives: affinity and efficacy at four subtypes of human adenosine receptors.
Biochem. Pharmacol., 68 (10): 1985-93. [PMID:15476669]
5. Jacobson KA, Gao ZG. (2006)
Adenosine receptors as therapeutic targets.
Nat Rev Drug Discov, 5 (3): 247-64. [PMID:16518376]
6. Kim J, Wess J, van Rhee AM, Schöneberg T, Jacobson KA. (1995)
Site-directed mutagenesis identifies residues involved in ligand recognition in the human A2a adenosine receptor.
J. Biol. Chem., 270 (23): 13987-97. [PMID:7775460]
7. Klotz KN, Hessling J, Hegler J, Owman C, Kull B, Fredholm BB, Lohse MJ. (1998)
Comparative pharmacology of human adenosine receptor subtypes - characterization of stably transfected receptors in CHO cells.
Naunyn Schmiedebergs Arch. Pharmacol., 357 (1): 1-9. [PMID:9459566]
8. 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]
9. Liang BT Urso R Sambraski E, Jacobson KA. (2010)
Adenosine A3 receptors in muscle protection.  In  Adenosine Receptors from Cell Biology to Pharmacology
Edited by Borea P (Springer) 257-280. [ISBN:9789048131440]
10. Linden J, Thai T, Figler H, Jin X, Robeva AS. (1999)
Characterization of human A(2B) adenosine receptors: radioligand binding, western blotting, and coupling to G(q) in human embryonic kidney 293 cells and HMC-1 mast cells.
Mol. Pharmacol., 56 (4): 705-13. [PMID:10496952]
11. Obiefuna PC, Batra VK, Nadeem A, Borron P, Wilson CN, Mustafa SJ. (2005)
A novel A1 adenosine receptor antagonist, L-97-1 [3-[2-(4-aminophenyl)-ethyl]-8-benzyl-7-{2-ethyl-(2-hydroxy-ethyl)-amino]-ethyl}-1-propyl-3,7-dihydro-purine-2,6-dione], reduces allergic responses to house dust mite in an allergic rabbit model of asthma.
J. Pharmacol. Exp. Ther., 315 (1): 329-36. [PMID:16020631]
12. Varani K, Merighi S, Gessi S, Klotz KN, Leung E, Baraldi PG, Cacciari B, Romagnoli R, Spalluto G, Borea PA. (2000)
[(3)H]MRE 3008F20: a novel antagonist radioligand for the pharmacological and biochemical characterization of human A(3) adenosine receptors.
Mol. Pharmacol., 57 (5): 968-75. [PMID:10779381]