Quinazolines as adenosine receptor antagonists: SAR and selectivity for A2B receptors

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 1, 2003, Pages 77-85

  Webb, Thomas R ^a   Lvovskiy, Dmitriy ^a   Kim, Soon Ai ^b   Ji, Xiao Duo ^b   Melman, Neli ^b   Linden, Joel ^c   Jacobson, Kenneth A ^a,b  

^a ChemBridge Research Laboratories   (United States)

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

^c UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 ETHYL 7 METHYLQUINAZOLYL 2 GUANIDINE; 4 HYDROXYQUINAZOLYL 2 GUANIDINE; 4 METHYL 6 METHOXYQUINAZOLYL 2 N METHYLGUANIDINE; 4 METHYL 7 ETHOXYQUINAZOLYL 2 N ACETYLGUANIDINE; 4 METHYL 7 METHOXYQUINAZOLYL 2 (2' AMINO 4' IMIDAZOLINONE); 4 METHYL 7 METHOXYQUINAZOLYL 2 N BENZOYLGUANIDINE; 4 METHYL 7 METHOXYQUINAZOLYL 2 N,N DIACETYLGUANIDINE; 4 METHYL 8 ETHOXYQUINAZOLYL 2 GUANIDINE; 4 METHYL 8 METHOXYQUINAZOLYL 2 GUANIDINE; 4 METHYL 8 METHYLQUINAZOLYL 2 GUANIDINE; 4 METHYLQUINAZOLYL 2 N BENZOYLGUANIDINE; 4 METHYLQUINAZOLYL 2 N PROPIONYLGUANIDINE; 4 METHYLQUINAZOLYL 2 N,N DIACETYLGUANIDINE; 4,6 DIMETHYLQUINAZOLYL 2 N PROPIONYLGUANIDINE; 4,6,7 TRIMETHYLQUINAZOLYL 2 N ACETYLGUANIDINE; 4,6,7 TRIMETHYLQUINAZOLYL 2 N,N DIPROPIONYLGUANIDINE; 4,6,8 TRIMETHYLQUINAZOLYL 2 GUANIDINE; 4,7 DIMETHYLQUINAZOLYL 2 N PROPIONYLGUANIDINE; 4,7 DIMETHYLQUINAZOLYL 2 N,N DIACETYLGUANIDINE; 6 METHOXY 4 METHYLQUINAZOLYL 2 N,N DIPROPIONYLGUANIDINE; ADENOSINE A2 RECEPTOR ANTAGONIST; ADENOSINE A2B RECEPTOR; CMB 6446; N (7 METHOXY 4 METHYLQUINOLIN 2 YL)ACETAMIDE; N (7 METHOXY 4 METHYLQUINOLIN 2 YL)CARBAMIC ACID METHYL ESTER; N (7 METHOXY 4 METHYLQUINOLIN 2 YL)GUANIDINE; N TERT BUTYLOXYCARBONYL N' (7 METHOXY 4 METHYLQUINOLIN 2 YL)GUANIDINE; N,N' DI TERT BUTYLOXYCARBONYL N' (7 METHOXY 4 METHYLQUINOLIN 2 YL)GUANIDINE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DATA BASE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; NONHUMAN; PHARMACOPHORE; RAT; RECEPTOR AFFINITY; RECEPTOR BLOCKING; STRUCTURE ACTIVITY RELATION;

ANIMALS; BRAIN; CELL LINE; CELL MEMBRANE; CORPUS STRIATUM; DATABASES, FACTUAL; HUMANS; QUINAZOLINES; RADIOLIGAND ASSAY; RATS; RECEPTOR, ADENOSINE A2B; RECEPTORS, PURINERGIC P1; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; TRITIUM;

EID: 0037413338     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(02)00323-1     Document Type: Article

References (21)

1. Jacobson, K. A.; Knutsen, L. J. S. In P1 and P2 Purine and Pyrimidine Receptors; Abbracchio, M. P., Williams, M., Eds.; Handbook of Experimental Pharmacology, Volume 151/I: Purinergic and Pyrimidinergic Signaling I; Springer: Berlin, Germany, 2001; p 129.
2. Jacobson, K. A.; Knutsen, L. J. S. In P1 and P2 Purine and Pyrimidine Receptors; Abbracchio, M. P., Williams, M., Eds.; Handbook of Experimental Pharmacology, Volume 151/I: Purinergic and Pyrimidinergic Signaling I; Springer: Berlin, Germany, 2001; p 129.
3. Kim Y.-C., Ji X.-D., Melman N., Linden J., Jacobson K. A. J. Med. Chem. 43:2000;1165.
4. Webb T. R., Melman N., Lvovskiy D., Ji X.-D., Jacobson K. A. Bioorg. Med. Chem. Lett. 10:2000;31.
5. Feoktistov I., Polosa R., Holgate S. T., Biaggioni I. Trends Pharmacol. Sci. 19:1998;148.
6. Kirshenbaum, A. S.; Hettinger, B.; Day, Y.-J.; Gilfillan, A. M.; Metcalfe, D. D.; Kim, Y.-C.; Linden, J.; Jacobson, K. A. 2001, Amer. Acad. Allergy, Asthma and Immunol., 57th Annual Meeting, 2001 (abstr 2000803).
7. Auchampach J. A., Jin J., Wan T. C., Caughey G. H., Linden J. Mol. Pharmacol. 52:1998;846.
8. Ji X.-D., Jacobson K. A. Drug Des. Discov. 16:1999;217.
9. Olah M. E., Gallo-Rodriguez C., Jacobson K. A., Stiles G. L. Mol. Pharmacol. 45:1994;978.
10. Cliffe W. H. J. Chem. Soc. 35:1933;1327.
11. Knövenagel E. Ber. 54B:1921;1722.
12. Shikhaliev Kh. S., Falaleyev A. V., Ermolova G. I., Solov'ev A. S. Chem. Heterocycl. Comp. 35:1999;818.
13. Shikhaliev Kh. S., Falaleyev A. V., Ermolova G. I., Solov'ev A. S. Khim. Khim. Tekhnol. 41:1998;116.
14. Fozard J. R., Hannon J. P. Pulm. Pharmacol. Ther. 12:1999;111.
15. Salvatore C. A., Tilley S. L., Latour A. M., Fletcher D. S., Koller B. H., Jacobson M. A. J. Biol. Chem. 275:2000;4429.
16. Feoktistov I., Polosa R., Holgate S.T., Biaggioni I. Trends Pharmacol. Sci. 19:1998;148.
17. Jacobson K. A., IJzerman A. P., Linden J. Drug Devel. Res. 47:1999;45.
18. Arya V. P., David J., Grewal R. S., Marathe S. B., Patil S. D. Indian J. Chem. 15B:1977;1129.
19. Rosowsky A., Nadel M. E., Modest E. J. J. Heterocycl. Chem. 9:1972;625.
20. van Muijlwijk-Koezen J. E., Timmerman H., Link R., van der Goot H., Ijerman A. P. J. Med. Chem. 41:1998;3994.
21. Feichtinger K., Zapf C., Sings H. L., Goodman M. J. Org. Chem. 63:1998;3804.