Synthesis of novel 1-alkyl-8-substituted-3-(3-methoxypropyl) xanthines as putative A2B receptor antagonists

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 9, 2009, Pages 3426-3432

  Nieto, María Isabel ^a   Balo, María Carmen ^b   Brea, José ^b   Caamaño, Olga ^b   Cadavid, María Isabel ^b   Fernández, Franco ^b   Mera, Xerardo García ^b   López, Carmen ^b   Rodríguez Borges, José Enrique ^c  

^a UNIVERSITY OF A CORUÑA   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^c UNIVERSITY OF PORTO   (Portugal)

Author keywords

1 Alkyl 8 substituted 3 (3 methoxypropyl) xanthines; Adenosine receptor antagonist; hA2B and hA2A Binding affinities; Structure affinity relationships

Indexed keywords

8 [4 [(CYCLOPENTYLCARBAMOYL)METHOXY]PHENYL] 1 ETHYL 3 (3 METHOXYPROPYL) 1H PURINE 2,6(3H,7H) DIONE; ADENOSINE A1 RECEPTOR; ADENOSINE A2A RECEPTOR; ADENOSINE A2B RECEPTOR; ADENOSINE A2B RECEPTOR ANTAGONIST; ADENOSINE A3 RECEPTOR; ADENOSINE RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG; XANTHINE DERIVATIVE;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; STRUCTURE ACTIVITY RELATION;

ADENOSINE A2 RECEPTOR ANTAGONISTS; HELA CELLS; HUMANS; PYRAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP; XANTHINES;

EID: 65249095631     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.03.029     Document Type: Article

References (27)

1. Gao Z.-G., and Jacobson K.A. Exp. Opin. Emerg. Drugs 12 (2007) 479
2. Burnstock G. Cell. Mol. Life Sci. 64 (2007) 1471
3. Jacobson K.A., and Gao Z.-G. Nat. Rev. Drug Disc. 5 (2006) 247
4. Fredholm B.B., Ijzerman A.P., Jacobson K.A., Klotz K.N., and Linden J. Pharmacol. Rev. 53 (2001) 527
5. Fossetta J., Deno G., Fan X., Du X.K., Soude-Bermejo A., De Bouteiller O., Caux C., Lunn C., Lundell D., and Palmer R.K. Mol. Pharmacol. 63 (2003) 342
6. Shneyvays V., Zinman T., and Shainberg A. Cell Calcium 36 (2004) 387
7. Berge M., Hylkeman M., Verslius M., and Pastma D.S. Drugs R&D 8 (2007) 13
8. Akkari R., Burbiel J.C., Hockemeyer J., and Mueller C.E. Curr. Top. Med. Chem. 6 (2006) 1375
9. Zhong H., Bellardinelli L., and Zeng D. Am. J. Resp. Cell Mol. Biol. 30 (2004) 118
10. Zhong H., Bellardinelli L., and Zeng D. Am. J. Resp. Cell Mol. Biol. 5 (2006) 587
11. Holgate S.T. Br. J. Pharmacol. 45 (2005) 1009
12. Jacobson K.A., Ijzerman A.P., and Linden J. Drug Dev. Res. 47 (1999) 45
13. Zhong H., Bellardinelli L., Moa T., and Zeng D. Am. J. Resp. Cell Mol. Biol. 32 (2004) 2
14. Beukers M., Meurs I., and Ijzerman A. Med. Res. Rev. 26 (2006) 667
15. Zoblocki J., Elzein E., and Kalla R. Exp. Opin. Ther. Patents 16 (2006) 1347
16. Cacciari B., Pastorin G., Bolcato C., Spalluto G., Bacilieri M., and Moro S. Mini-Rev. Med. Chem. 5 (2005) 1053
17. Baraldi P.G., Tabrizi M.A., Preti D., Bovero A., Romagnoli R., Fruttarolo F., Zaid N.A., Moorman A.R., Varani K., Gessi S., Merighi S., and Borea P.A. J. Med. Chem. 47 (2004) 1434
18. Elzien E., Kalla R.V., Perry T., Gimbel A., Zeng D., Lusting D., Leung K., and Zablocki J. J. Med. Chem. 51 (2008) 2267
19. Daly J.W., Padgett W., Shamim M.T., Butts-Lamb P., and Waters J. J. Med. Chem. 28 (1985) 487-492
20. Kim Y.-C., Karton Y., Ji X.-D., Melman N., Linden J., and Jacobson K.A. Drug Dev. Rev. 47 (1999) 178
21. Kim Y.-C., Ji X.-D., Melman N., Linden J., and Jacobson K.A. J. Med. Chem. 43 (2000) 1165
22. Papesch V., and Schroeder E.F. J. Org. Chem. 16 (1951) 1879
23. Mohareb R.M., Habashi A., Ibrahim N.S., and Sherif S.M. Synthesis (1987) 228
24. Kim S.-A., Marshall M.A., Melman N., Ibrahim N.S., Kim H.S., Müller C.E., Linden J., and Jacobson K.A. J. Med. Chem. 45 (2002) 2131
25. Fortes C.C., and Garrote C.F.D. Synth. Commun. 27 (1997) 2993
26. Balo M.C., López C., Brea J.M., Fernández F., and Caamaño O. Chem. Pharm. Bull. 55 (2007) 372
27. Touchstone J. Advances in Thin-Layer Chromatography (1982), Wiley, New York