2,6-Disubstituted and 2,6,8-trisubstituted purines as adenosine receptor antagonists

Journal of Medicinal Chemistry

Volumn 49, Issue 10, 2006, Pages 2861-2867

  Chang, Lisa C W ^a   Spanjersberg, Ronald F ^a   Von Frijtag Drabbe Künzel, Jacobien K ^a   Mulder Krieger, Thea ^a   Brussee, Johannes ^a   Ijzerman, Adriaan P ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

8 CYCLOPENTYL 2,6 DIPHENYLPURINE; ADENOSINE A1 RECEPTOR; ADENOSINE RECEPTOR BLOCKING AGENT; LUF 5962; PURINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG RECEPTOR BINDING; DRUG STRUCTURE; HYDROGEN BOND; PHARMACOPHORE; STRUCTURE ACTIVITY RELATION;

ANIMALS; CELL LINE; CRICETINAE; CRICETULUS; HUMANS; PURINES; RADIOLIGAND ASSAY; RECEPTOR, ADENOSINE A1; RECEPTOR, ADENOSINE A2A; RECEPTOR, ADENOSINE A3; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33646737062     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050640i     Document Type: Article

References (28)

1. Fredholm, B. B.; IJzerman, A. P.; Jacobson, K. A.; Klotz, K.-N.; Linden, J. M. International union of pharmacology. XXV. Nomenclature and classification of adenosine receptors.Pharmacol. Rev. 2001, 53, 527-552.
2. 1 receptor antagonists. J. Med. Chem. 2004, 47, 6529-6540.
3. 1 receptor. Chem. Biodiversity 2004, 1, 1591-1626.
4. 6-substituted 9-methyladenines: a new class of adenosine receptor antagonists. FEBS Lett. 1987, 215, 203-208.
5. 1 adenosine receptor. J. Med. Chem. 1991, 34, 2877-2882.
6. 1 receptor antagonists. J. Med. Chem. 1997, 40, 3765-3772.
7. 1 adenosine receptors. Drug Dev. Res. 2001, 54, 52-65.
8. Klotz, K.-N.; Kachler, S.; Lambertucci, C.; Vittori, S.; Volpini, R.; Cristalli, G. 9-Ethyladenine derivatives as adenosine receptor antagonists: 2- and 8-substitution results in distinct selectivities. Naunyn-Schmiedeberg's Arch. Pharmacol. 2003, 367, 629-634.
9. 1 receptor. Bioorg. Med. Chem. 2004, 12, 139-149.
10. Gundersen, L. L. 6-Chloropurines and organostannanes in palladium catalyzed cross coupling reactions. Tetrahedron Lett. 1994, 35, 3155-3158.
11. Gundersen, L. L.; Langli, G.; Rise, F. Regioselective Pd-mediated coupling between 2,6-dichloropurines and organometallic reagents. Tetrahedron Lett. 1995, 36, 1945-1948.
12. Gundersen, L. L.; Nissen-Meyer, J.; Spilsberg, B. Synthesis and antimycobacterial activity of 6-arylpurines: the requirements for the N-9 substituent in active antimycobacterial purines. J. Med. Chem. 2002, 45, 1383-1386.
13. Hocek, M.; Hockova, D.; Dvorakova, H. Dichotomy in regioselective cross-coupling reactions of 6,8-dichloropurines with phenylboronic acid and methylmagnesium chloride: Synthesis of 6,8-disubstituted purines. Synthesis 2004, 889-894.
14. Havelkova, M.; Dvorak, D.; Hocek, M. The Suzuki-Miyaura cross-coupling reactions of 2-, 6- or 8-halopurines with boronic acids leading to 2-, 6- or 8-aryl- and -alkenylpurine derivatives. Synthesis 2001, 1704-1710.
15. Hocek, M. Syntheses of purines bearing carbon substituents in positions 2, 6 or 8 by metal- or organometal-mediated C-C bond-forming reactions. Eur. J. Org. Chem. 2003, 2, 245-254.
16. Hocek, M.; Holy, A.; Votruba, I.; Dvorakova, H. Synthesis and cytostatic activity of substituted 6-phenylpurine bases and nucleosides: application of the Suzuki-Miyaura cross-coupling reactions of 6-chloropurine derivatives with phenylboronic acids. J. Med. Chem. 2000, 43, 1817-1825.
17. Langli, G.; Gundersen, L. L.; Rise, F. Regiochemistry in Stille couplings of 2,6-dihalopurines. Tetrahedron 1996, 52, 5625-5638.
18. 1 adenosine receptors. Farmaco 1997, 52, 61-65.
19. 1 adenosine receptor ligands. A comparison with the corresponding adenines and 8-azaadenines. Eur. J. Med. Chem. 2003, 38, 983-990.
20. 1 adenosine receptors and adenosine deaminase. Farmaco 2002, 57, 221-233.
21. Antonini, I.; Cristalli, G.; Franchetti, P.; Grifantini, M.; Martelli, S.; Petrelli, F. Deaza analogues of adenosine as inhibitors of blood platelet aggregation. J. Pharm. Sci. 1984, 73, 366-369.
22. Young, R. C.; Jones, M.; Milliner, K. J.; Rana, K. K.; Ward, J. G. Purine derivatives as competitive inhibitors of human erythrocyte membrane phosphatidylinositol 4-kinase. J. Med. Chem. 1990, 33, 2073-2080.
23. 1 adenosine receptors. J. Med. Chem. 1994, 37, 2704-2712.
24. 3 receptor ligands. II. Structure affinity profile of a series of isoquinoline and quinazoline compounds. J. Med. Chem. 1998, 41, 3994-4000.
25. 3 receptor. J. Med. Chem. 2000, 43, 2227-2238.
26. 1 adenosine receptors stably expressed in Chinese hamster ovary cells. Mol. Pharmacol. 1998, 53, 886-893.
27. Cassidy, F.; Olsen, R. K.; Robins, R. K. Aromaticity in heterocyclic systems. V. Bromination studies of certain purines, pyrrolo[3,2-d]-pyrimidines, and pyrazolo[4,3-d]pyrimidines. J. Heterocycl. Chem. 1968, 5, 461-465.
28. Hocek, M.; Dvorakova, H. An efficient synthesis of 2-substituted 6-methylpurine bases and nucleosides by Fe- or Pd-catalyzed cross-coupling reactions of 2,6-dichloropurines. J. Org. Chem. 2003, 68, 5773-5776.