Synthesis and biological evaluation of 2-alkynyl-N6-methyl- 5′-N-methylcarboxamidoadenosine derivatives as potent and highly selective agonists for the human adenosine A3 receptor

Journal of Medicinal Chemistry

Volumn 52, Issue 23, 2009, Pages 7897-7900

  Volpini, Rosaria ^a   Buccioni, Michela ^a   Dal Ben, Diego ^a   Lambertucci, Catia ^a   Lammi, Carmen ^a   Marucci, Gabriella ^a   Ramadori, Anna T ^a   Klotz, Karl Norbert ^b   Cristalli, Gloria ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 PYRIDINYL)ETHYNYL N6 METHYL 5' N METHYLCARBOXAMIDOADENOSINE; 2 (4 ACETYLPHENYL)ETHYNYL N6 METHYL 5' N METHYLCARBOXAMIDOADENOSE; 2 (4 FLUOROPHENYL)ETHYNYL N6 METHYL 5' N METHYLCARBOXAMIDOADENOSINE; ADENOSINE A2 RECEPTOR; ADENOSINE A3 RECEPTOR; ADENOSINE A3 RECEPTOR AGONIST; ADENOSINE DERIVATIVE; N6 METHYL 2 PHENYLETHYL 5' N METHYLCARBOXAMIDOADENOSINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; ISOTOPE LABELING; LIGAND BINDING; NONHUMAN; PROTEIN DETERMINATION; PROTEIN FUNCTION; RADIOASSAY; RECEPTOR AFFINITY;

EID: 72249085783     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900754g     Document Type: Article

References (12)

1. Fredholm, B. B.; IJzerman, A. P.; Jacobson, K. A.; Klotz, K. N.; Linden, J. International Union of Pharmacology. XXV. Nomenclature and classification of adenosine receptors. Pharmacol. Rev. 2001, 53, 527-552.
2. Cristalli, G.; Volpini, R. Adenosine receptors: chemistry and pharmacology. Curr. Top. Med. Chem. 2003, 3, 355-469.
3. Englert, M.; Quitterer, U.; Klotz, K. N. Effector coupling of stably transfected human A3 adenosine receptors in CHO cells. Biochem. Pharmacol. 2002, 64, 61-65.
4. Jacobson, K. A.; Gao, Z. G. Adenosine receptors as therapeutic targets. Nat. Rev. Drug. Discovery 2006, 5, 247-264.
5. Volpini, R.; Costanzi, S.; Lambertucci, C.; Vittori, S.; Cristalli, G. Purine nucleosides bearing 1-alkynyl chains as adenosine receptor agonists. Curr. Pharm. Des. 2002, 8, 2285-2298.
6. Cristalli, G.; Camaioni, E.; Costanzi, S.; Vittori, S.; Volpini, R.; Klotz, K. N. Characterization of potent ligands at human recombinant adenosine receptors. Drug Dev. Res. 1998, 45, 176-181.
7. Cristalli, G.; Camaioni, E.; Vittori, S.; Volpini, R.; Borea, P. A.; Conti, A.; Dionisotti, S.; Ongini, E.; Monopoli, A. 2-Aralkynyl and 2-heteroalkynyl derivatives of adenosine-50-N-ethyluronamide as selective A2A adenosine receptor agonists. J. Med. Chem. 1995, 38, 1462-1472.
8. Volpini, R.; Dal Ben, D.; Lambertucci, C.; Taffi, S.; Vittori, S.; Klotz, K. N.; Cristalli, G. N6-Methoxy-2-alkynyladenosine derivatives as highly potent and selective ligands at the human A3 adenosine receptor. J. Med. Chem. 2007, 50, 1222-1230.
9. Volpini, R.; Costanzi, S.; Lambertucci, C.; Taffi, S.; Vittori, S.; Klotz, K. N.; Cristalli, G. N6-Alkyl-2-alkynyl derivatives of adenosine as potent and selective agonists at the human adenosine A3 receptor and a starting point for searching A2B ligands. J. Med. Chem. 2002, 45, 3271-3279.
10. Cristalli, G.; Eleuteri, A.; Vittori, S.; Volpini, R.; Lohse, M. J.; Klotz, K. N. 2-Alkynyl derivatives of adenosine and adenosine-50- N-ethyluronamide as selective agonists at A2 adenosine receptors. J. Med. Chem. 1992, 35, 2363-2368.
11. Cristalli, G.; Volpini, R.; Vittori, S.; Camaioni, E.; Monopoli, A.; Conti, A.; Dionisotti, S.; Zocchi, C.; Ongini, E. 2-Alkynyl derivatives of adenosine-50-N-ethyluronamide: selective A2 adenosine receptor agonists with potent inhibitory activity on platelet aggregation. J. Med. Chem. 1994, 37, 1720-1726.
12. Klotz, K. N.; Hessling, J.; Hegler, J.; Owman, C.; Kull, B.; Fredholm, B. B.; Lohse, M. J. Comparative pharmacology of human adenosine receptor subtypes: characterization of stably transfected receptors in CHO cells. Naunyn-Schmiedeberg's Arch. Pharmacol. 1998, 357, 1-9.