Water-soluble phosphate prodrugs of 1-propargyl-8-styrylxanthine derivatives, A2(A)-selective adenosine receptor antagonists

Journal of Medicinal Chemistry

Volumn 43, Issue 3, 2000, Pages 440-448

  Sauer, Roland ^a   Maurinsh, Juris ^b,c   Reith, Ulrike ^a   Fülle, Friederike ^a   Klotz, Karl Norbert ^b   Müller, Christa E ^a,b,d  

^a UNIVERSITY OF BONN   (Germany)

^b UNIVERSITY OF WÜRZBURG   (Germany)

^c LATVIAN INSTITUTE OF ORGANIC SYNTHESIS   (Latvia)

^d Pharmazeutisches Institut   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ADENOSINE RECEPTOR BLOCKING AGENT; HETEROCYCLIC COMPOUND; PRODRUG; SODIUM HYDROXIDE; URACIL DERIVATIVE; XANTHINE DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; NONHUMAN; PHOSPHORYLATION; RAT;

ANIMALS; CAUDATE NUCLEUS; CEREBRAL CORTEX; CHO CELLS; CORPUS STRIATUM; CRICETINAE; HUMANS; PRODRUGS; RADIOLIGAND ASSAY; RATS; RECEPTOR, ADENOSINE A2A; RECEPTORS, PURINERGIC P1; RECOMBINANT PROTEINS; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; XANTHINES;

EID: 0034628545     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9911480     Document Type: Article

References (33)

1. 2A-Selective adenosine receptor antagonists: development of water-soluble prodrugs and a new tritiated radioligand. Drug Dev. Res. 1998, 45, 190-197.
2. Ralevic, V.; Burnstock G. Receptors for purines and pyrimidines. Pharmacol. Rev. 1998, 50, 413-492.
3. Ongini, E.; Dionisotti, S.; Morelli, M.; Ferré, S.; Svenningsson, P.; Fuxe, K.; Fredholm, B. B. Neuropharmacology of the adenosine A2A receptors. Drug Dev. Res. 1996, 39, 450-460.
4. 2A receptors in the caudate-putamen. Neuroreport 1998, 9, 1803-1806.
5. 2A receptors. Trends Pharmacol. Sci. 1996, 17, 364-372.
6. 2A receptor antagonists as new agents for the treatment of Parkinson's disease. Trends Pharmacol. Sci. 1997, 18, 338-344.
7. Snyder, S. H. Knockouts anxious for new therapy. Nature 1997, 388, 624.
8. 2A adenosine receptor antagonists. Curr. Med. Chem. 1995, 2, 707-722.
9. Müller, C. E.; Stein, B. Adenosine receptor antagonists: structures and potential therapeutic applications. Curr. Pharm. Des. 1996, 2, 501-530.
10. Poulsen, S. A.; Quinn, R. J. Adenosine receptors: new opportunities for future drugs. Bioorg. Med. Chem. 1998, 6, 619-641.
11. 2A-Selective adenosine receptor antagonists. J. Med. Chem. 1997, 40, 4396-4405.
12. 2A-selective adenosine receptor antagonists. Bioorg. Med. Chem. 1998, 6, 707-719.
13. 2A adenosine receptor antagonists. Eur. J. Med. Chem. 1997, 32, 709-719.
14. Jacobson, K. A.; Gallo-Rodriguez, C.; Melman, N.; Fischer, B.; Maillard, M.; van Bergen, A.; van Galen, P. J. M.; Karton, Y. Structure-activity relationships of 8-styrylxanthines as A2-selective adenosine receptor antagonists. J. Med. Chem. 1993, 36, 1333-1342.
15. Roche, E. B., Ed. Bioreversible carriers in drug design - theory and application; Pergamon Press: New York, Oxford, 1987.
16. Jungheim, L. N.; Shepherd, T. A. Design of antitumor pro-drugs: substrates for antibody targeted enzymes. Chem. Rev. 1994, 94, 1553-1566.
17. Cho, M. J.; Kurtz, R. R.; Lewis, C.; Machkovech, S. M.; Houser, D. J. Metronidazole phosphate - a water-soluble prodrug for parenteral solutions of metronidazole. J Pharm. Sci. 1982, 71, 410-414.
18. Varia, S. A.; Schuller, S.; Sloan, K. B.; Stella, V. J. Phenytoin prodrugs III: water-soluble prodrugs for oral and/or parenteral use. J. Pharm. Sci. 1984, 8, 1068-1080.
19. Chong, K.-T.; Ruwart, M. J.; Hinshaw, R. R.; Wilkinson, K. F.; Rush, B. D.; Yancey, M. F.; Strohbach, J. W.; Thaisrivongs, S. Peptidometic HIV protease inhibitors: phosphate prodrugs with improved biological activities. J. Med. Chem. 1993, 36, 2575-2577.
20. Müller, C. E.; Sandoval-Ramirez, J. A. A new versatile synthesis of xanthines with variable substituents in the 1-, 3-, 7-and 8-positions. Synthesis 1995, 1295-1299.
21. Hipp, J.; Müller, C. E. Unpublished.
22. Slotin, L. A. Current Methods of phosphorylation of biological molecules. Synthesis 1976, 737-752.
23. Perich, J. W.; Johns, R. B. Di-tert.-butyl-N,N-diethylphosphoramidite. A new phosphitylating agent for the efficient phosphorylation of alcohols. Synthesis 1988, 142-144.
24. Roth, H. J.; Eger, K.; Troschütz, R. Pharmaceutical chemistry, Vol. 2: Drug analysis: Ellis Horwood: Chichester, 1991.
25. Müller, C. E. Synthesis of 3-substituted 6-aminouracils. Tetrahedron Lett. 1991, 32, 6539-6540.
26. 2A-adenosine receptor antagonists. Arch. Pharm. Pharm. Med. Chem. 1997, 330, 181-189.
27. 2 receptors in rat brain. J. Pharmacol. Exp. Ther. 1989, 251, 888-893.
28. 3H]phenylxanthine. Proc. Natl. Acad. Sci. U.S.A. 1980, 77, 5547-5551.
29. Klotz, K. N.; Hessling, J.; Hegler, J.; Owman, C.; Fredholm, B. B.; Lohse, M. J. Comparative pharmacology of human adenosine receptors in CHO cells. Naunyn Schmiedeberg's Arch. Pharmacol. 1998, 357, 1-9.
30. 3H]CGS 21680 to human and rat brain: evidence for multiple affinity sites. J. Neurochem. 1990, 55, 1763-1771.
31. 1 adenosine receptors. Naunyn-Schmiedeberg's Arch. Pharmacol. 1989, 340, 679-683.
32. 2A adenosine receptors. Eur. J. Pharm. Sci., in press.
33. Matuszczak, B.; Pekala, E.; Müller, C. E. 1-Substituted 4-[chloropyrazolyl][1, 2, 4]triazolo [4,3-a]quinoxalines: synthesis and structure-activity relationships of a new class of benzodiazepine and adenosine receptor ligands. Arch. Pharm. Pharm. Med. Chem. 1998, 331, 163-169.