2-Phenylimidazo[2,1-i]purin-5-ones: Structure-activity relationships and characterization of potent and selective inverse agonists at human A3 adenosine receptors

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 3, 2003, Pages 347-356

  Ozola, Vita ^a   Thorand, Mark ^a   Diekmann, Martina ^a   Qurishi, Ramatullah ^a   Schumacher, Britta ^a   Jacobson, Kenneth A ^b   Müller, Christa E ^a  

^a UNIVERSITY OF BONN   (Germany)

^b NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (3,4 DICHLOROPHENYL) 8 ETHYL 9 METHYL 4 PROPYL 4,5,7,8 TETRAHYDRO 1H IMIDAZO[2,1 I]PURIN 5 ONE; 2 PHENYLIMIDAZOPURINONE; 4 METHYL 2 PHENYLIMIDAZOPURINONE; 4,9 DIMETHYL 8 ETHYL 2 (2,3,5 TRICHLOROPHENYL) 4,5,7,8 TETRAHYDRO 1H IMIDAZO[2,1 I]PURIN 5 ONE; 8 ETHYL 2 PHENYL 4 PROPYL 4,5,7,8 TETRAHYDRO 1H IMIDAZO[2,1 I]PURIN 5 ONE; 8 ETHYL 4 METHYL 2 (2,3,5 TRICHLOROPHENYL) 4,5,7,8 TETRAHYDRO 1H IMIDAZO[2,1 I]PURIN 5 ONE; ADENOSINE A2A RECEPTOR; ADENOSINE A3 RECEPTOR; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); IMIDAZOLINE; PURINE DERIVATIVE; UNCLASSIFIED DRUG;

ADULT; ANIMAL CELL; ANIMAL TISSUE; ARTICLE; CASE REPORT; CELL MEMBRANE; CHLORINATION; CHO CELL; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SOLUBILITY; ENANTIOMER; HUMAN; HUMAN CELL; HUMAN TISSUE; MALE; METHYLATION; NONHUMAN; RAT; RECEPTOR AFFINITY; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

ANIMALS; BENZENE DERIVATIVES; BRAIN; CELL MEMBRANE; CHO CELLS; CRICETINAE; HUMANS; HYDROCARBONS, CHLORINATED; HYDROGEN-ION CONCENTRATION; IMIDAZOLES; LIGANDS; PURINONES; RADIOLIGAND ASSAY; RATS; RECEPTOR, ADENOSINE A3; RECEPTORS, PURINERGIC P1; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

CRICETINAE; CRICETULUS GRISEUS;

EID: 0037295346     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(02)00456-X     Document Type: Article

References (29)

1. Ralevic V., Burnstock G. Pharmacol. Rev. 50:1998;413.
2. Müller C.E. Mini-Reviews Med. Chem. 1:2001;433.
3. Kim Y.-C., Ji X., Jacobson K.A. J. Med. Chem. 39:1996;4142.
4. Kim Y.-C., de Zwart M., Chang L., Moro S., von Frijtag Drabbe Künzel J.K., Melman N., IJzerman A.P., Jacobson K.A. J. Med. Chem. 41:1998;2835.
5. Baraldi P.G., Cacciari B., Romagnoli R., Spalluto G., Klotz K.-N., Leung E., Varani K., Gessi S., Merighi S., Borea P.A. J. Med. Chem. 42:1999;4473.
6. Varani K., Merighi S., Gessi S., Klotz K.-N., Leung E., Baraldi P.G., Cacciari B., Romagnoli R., Spalluto G., Borea P.A. Mol. Pharmacol. 57:2000;968.
7. Van Muijlwijk-Koezen J.E., Timmerman H., Link R., van der Goot H., IJzerman A.P. J. Med. Chem. 41:1998;3987.
8. Van Muijlwijk-Koezen J.E., Timmerman H., Link R., van der Goot H., IJzerman A.P. J. Med. Chem. 41:1998;3994.
9. Van Muijlwijk-Koezen J.E., Timmerman H., van der Goot H., Menge W.M., Frijtag von Drabbe Künzel J., de Groote M., IJzerman A.P. J. Med. Chem. 43:2000;2227.
10. Jiang J., van Rhee A.M., Melman N., Ji X., Jacobson K.A. J. Med. Chem. 39:1996;4667.
11. Jiang J., van Rhee A.M., Chang L., Patchornik A., Ji X., Evans P., Melman N., Jacobson K.A. J. Med. Chem. 40:1997;2596.
12. Suzuki F., Shimada J., Nonaka H., Ishii A., Shiozaki S., Ichikawa S., Ono E. J. Med. Chem. 35:1992;3578.
13. Müller C.E., Thorand M., Qurishi R., Dieckmann M., Jacobson K.A., Padgett W.L., Daly J.W. J. Med. Chem. 45:2002;3440.
14. Hipp, J. Dissertation, University of Würzburg, 1997.
15. Shimada J., Kuroda T., Suzuki F. J. Heterocyclic Chem. 30:1993;241.
16. Tsumuki, H.; Saki, M.; Nonaka, H.; Ichimura, M.; Shimada, J.; Suzuki, F.; Ichikawa, S.; Kosaka, N. Kyowa Hakko Kogyo Co., Ltd., Japan, World Patent WO98/15555, 1998.
17. Saki M., Tsumuki H., Nonaka H., Shimada J., Ichimura M. Eur. J. Pharmacol. 444:2002;133.
18. Hayallah A.M., Sandoval-Ramirez J., Reith U., Schobert U., Preiss B., Schumacher B., Daly J.W., Müller C.E. J. Med. Chem. 45:2002;1500.
19. Müller C.E., Diekmann M., Thorand M., Ozola V. Bioorg. Med. Chem. Lett. 12:2002;501.
20. Müller C.E. Exp. Opin. Ther. Patents. 7:1997;419.
21. Van Rhee A.M., Jiang J.-L., Melman N., Olah M.E., Stiles G.L., Jacobson K.A. J. Med. Chem. 41:1998;3186.
22. Geis U., Grahner B., Pawłowski M., Drabczynska A., Gorczyca M., Müller C.E. Pharmazie. 50:1995;333.
23. Lorenzen A., Fuss M., Vogt H., Schwabe U. Mol. Pharmacol. 44:1993;115.
24. Shryock J.C., Ozeck M.J., Belardinelli L. Mol. Pharmacol. 53:1998;886.
25. De Ligt R.A.F., Kourounakis A.P., IJzerman A.P. Br. J. Pharmacol. 130:2000;1.
26. Hess S., Müller C.E., Frobenius W., Reith U., Klotz K.-N., Eger K.J. Med. Chem. 43:2000;4636.
27. Müller C.E., Maurinsh J., Sauer R. Eur. J. Pharm. Sci. 10:2000;259.
28. Klotz K.-N., Hessling J., Hegler J., Owman C., Kull B., Fredholm B.B., Lohse M.J. Naunyn-Schmiedberg's Arch. Pharmacol. 357:1998;1.
29. Sauer, R.; Maurinsh, J.; Reith, U.; Fülle, F.; Klotz, K.-N.; Müller, C. E. J. Med. Chem., 2000, 43, 440.