Discovery of potent and selective bicyclic A2B adenosine receptor antagonists via bioisosteric amide replacement

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 5, 2010, Pages 1634-1637

  Eastwood, Paul ^a   Gonzalez, Jacob ^a   Paredes, Sergio ^a   Fonquerna, Silvia ^a   Cardús, Arantxa ^a   Alonso, Juan Antonio ^a   Nueda, Arsenio ^a   Domenech, Teresa ^a   Reinoso, Raquel F ^a   Vidal, Bernat ^a  

^a Almirall SA ^*  (Spain)

Author keywords

A2B; Adenosine; Adenosine receptor antagonists; Amide bioisosteres; Asthma

Indexed keywords

ADENOSINE RECEPTOR A2B BLOCKING AGENT; ADENOSINE RECEPTOR BLOCKING AGENT; AMIDE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; DEPROTECTION REACTION; DRUG BIOAVAILABILITY; DRUG METABOLISM; DRUG SELECTIVITY; LIVER MICROSOME; NONHUMAN; PLASMA CLEARANCE; RAT; STEREOCHEMISTRY;

AMIDES; ANIMALS; ANTI-INFLAMMATORY AGENTS; BICYCLO COMPOUNDS; DRUG DISCOVERY; HUMANS; MICROSOMES, LIVER; NADP; RATS; RECEPTOR, ADENOSINE A2B;

EID: 76649097306     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.01.077     Document Type: Article

References (27)

1. Feoktistov I., and Biaggioni I. J. Clin. Invest. 96 (1995) 1979
2. Linden J. J. Clin. Invest. 116 (2006) 1835
3. Feoktistov I., Goldstein A.E., Ryzhov S., Zeng D., Belardinelli L., Voyno-Yasenetskaya T., and Biaggioni I. Circ. Res. 90 (2002) 531
4. Feoktistov I., Ryzhov S., Goldstein A.E., and Biaggioni I. Circ. Res. 91 (2003) 485
5. Feoktistov I., Ryzhov S., Zhong H., Goldstein A.E., Matafonov A., Zeng D., and Biaggioni I. Hypertension 44 (2004) 649
6. Rees D.A., Lewis B.M., Lewis M.D., Francis K., Scanlon M.F., and Ham J. Br. J. Pharmacol. 140 (2003) 764
7. Zhong H., Wu Y., Belardinelli L., and Zeng D. Am. J. Respir. Cell Mol. Biol. 35 (2006) 587
8. Novitskiy S., Ryzhov S., Zaynagetdinov R., Goldstein A., Huang Y., Tikhomirov O., Blackburn M., Biaggioni I., Carbone D., Feoktistov I., and Dikov M. Blood 112 (2008) 1822
9. Ryzhov S., Zaynagetdinov R., Goldstein A., Novitskiy S., Dikov M., Blackburn M., Biaggioni I., and Feoktistov I. J. Immunol. 180 (2008) 7212
10. Ryzhov S., Zaynagetdinov R., Goldstein A., Novitskiy S., Blackburn M., Biaggioni I., and Feoktistov I. J. Pharmacol. Exp. Ther. 324 (2008) 694
11. For recent reviews, see:. Caruso M., Varani K., Tringali G., and Polosa R. Curr. Med. Chem. 16 (2009) 3875
12. Haskó G., Csóka B., Németh Z.H., Vizi E.S., and Pacher P. Trends Immunol. 30 (2009) 263
13. Haskó G., Linden J., Cronstein B., and Pacher P. Nat. Rev. Drug Disc. 7 (2008) 759
14. Ham J., and Rees D. Endocr. Metab. Immune Disord. Drug Targets 8 (2008) 244
15. Beukers M.W., Meurs I., and Ijzerman A.P. Med. Res. Rev. 26 (2006) 667
16. Zablocki J., Elzein E., and Kalla R. Expert Opin. Ther. Pat. 16 (2006) 1347
17. Cacciari B., Pastorin G., Bolcato C., Spalluto G., Bacilieri M., and Moro S. Mini-Rev. Med. Chem. 5 (2005) 1053
18. Jacobson K.A., and Gao Z.-G. Nat. Rev. Drug Disc. (2006) 247
19. Eastwood, P.; Gonzalez, J.; Paredes, S.; Nueda, A.; Domenech T.; Alberti, J.; Vidal, B. Bioorg. Med. Chem. Lett., in press.
20. Vidal, B.; Eastwood, P.; Gonzalez, J. PCT Int. Appl. WO2005100353, 2005.
21. Chen P., Barrish J.C., Iwanowicz E., Lin J., Bednarz M.S., and Chen B.-C. Tetrahedron Lett. 42 (2001) 4293
22. Almansa, C.; Virgili, M. PCT Int. Appl. WO 2004076450, 2004.
23. Rodriguez A.L., Koradin C., Dohle W., and Knochel P. Angew. Chem., Int. Ed. 39 (2000) 2488
24. Chinchilla R., and Najera C. Chem. Rev. 107 (2007) 874
25. For details of the binding assays, see:. Vidal B., Nueda A., Esteve C., Domenech T., Benito S., Reinoso R.F., Pont M., Calbet M., López R., Cadavid M.I., Loza M.I., Cárdenas A., Godessart N., Beleta J., Warrellow G., and Ryder H. J. Med. Chem. 50 (2007) 2732
26. 2B receptor) indicated that these compounds are acting as antagonists. Further details can be found in Ref. 11.
27. Kalgutkar A.S., Gardner I., Obach R.S., Shaffer C.L., Callegari E., Henne K.R., Mutlib A.E., Dalvie D.K., Lee J.S., Nakai Y., O'Donnell J.P., Boer J., and Harriman S.P. Curr. Drug Metab. 6 (2005) 161