Design, synthesis, and biological evaluation of novel 4-alkylamino-1- hydroxymethylimidazo[1,2-a]quinoxalines as adenosine A 1 receptor antagonists

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 17, 2004, Pages 4701-4707

  Liu, Chun He ^a   Wang, Bo ^a   Li, Wei Zhang ^a   Yun, Liu Hong ^a   Liu, Ying ^a   Su, Rui Bing ^a   Li, Jin ^a   Liu, He ^a  

^a BEIJING INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY   (China)

Author keywords

Adenosine A 1 receptor; Imidazo 1,2 a quinoxaline; Tricyclic heteroaromatic compounds

Indexed keywords

1 (3 CHLOROQUINOXALIN 2 AMINO) 3 (TETRAHYDROPYRAN 2 YLOXY)PROPAN 2 OL; 1 (3 CHLOROQUINOXALIN 2 AMINO) 3 (TETRAHYDROPYRAN 2 YLOXY)PROPAN 2 ONE; 1 (3,6,7 TRICHLOROQUINOXALIN 2 AMINO) 3 (TETRAHYDROPYRAN 2 YLOXY)PROPAN 2 OL; 1 (3,6,7 TRICHLOROQUINOXALIN 2 AMINO) 3 (TETRAHYDROPYRAN 2 YLOXY)PROPAN 2 ONE; 1 (6,7 DIMETHYL 3 CHLOROQUINOXALIN 2 AMINO) 3 (TETRAHYDROPYRAN 2 YLOXY)PROPAN 2 OL; 1 (6,7 DIMETHYL 3 CHLOROQUINOXALIN 2 AMINO) 3 (TETRAHYDROPYRAN 2 YLOXY)PROPAN 2 ONE; 1 AMINO 3 (TETRAHYDROPYRAN 2 YLOXY)PROPAN 2 OL; 1 HYDROXYMETHYL 4 [2 (MORPHOLINO 4 YL)ETHYL]AMINOIMIDAZOL[1,2 A]QUINOXALINE; 1 HYDROXYMETHYL 4 ISOBUTYLAMINOIMIDAZO[1,2 A]QUINOXALINE; 1 HYDROXYMETHYLIMIDAZO[1,2 A]QUINOXALIN 4 ONE; 4 AMYLAMINO 7,8 DIMETHYL 1 HYDROXYMETHYLIMIDAZO[1,2 A]QUINOXALINE; 4 BENZYLAMINO 7,8 DICHLORO 1 HYDROXYMETHYLIMIDAZO[1,2 A]QUINOXALINE; 4 BENZYLAMINO 7,8 DIMETHYL 1 HYDROXYMETHYLIMIDAZO[1,2 A]QUINOXALINE; 4 BUTYLAMINO 7,8 DICHLORO 1 HYDROMETHYLIMIDAZO[1,2 A]QUINOXALINE; 4 CYCLOHEXYLAMINO 1 HYDROXYMETHYLIMIDAZO[1,2 A]QUINOXALINE; 4 CYCLOHEXYLAMINO 7,8 DICHLORO 1 HYDROMETHYLIMIDAZO[1,2 A]QUINOXALINE; 4 CYCLOPENTYLAMINO 1 HYDROXYMETHYLIMIDAZO[1,2 A]QUINOXALINE; 4 CYCLOPENTYLAMINO 7,8 DICHLORO 1 HYDROXYMETHYLIMIDAZO[1,2 A]QUINOXALINE; 4 CYCLOPENTYLAMINO 7,8 DIMETHYL 1 HYDROMETHYLIMIDAZO[1,2 A]QUINOXALINE; 7,8 DICHLORO 1 HYDROMETHYL 4 [2 (PYRROLIDIN 1 YL)ETHYL]AMINOIMIDAZO[1,2 A]QUINOXALINE; 7,8 DICHLORO 1 HYDROXYMETHYL 4 [2 (MORPHOLINO 4 YL)ETHYL]AMINOIMIDAZO[1,2 A]QUINOXALINE; 7,8 DICHLORO 1 HYDROXYMETHYL 4 ISOBUTYLAMINOIMIDAZO[1,2 A]QUINOXALINE; 7,8 DICHLORO 1 HYDROXYMETHYLIMIDAZO[1,2 A]QUINOXALIN 4 ONE; 7,8 DICHLORO 4 (3 DIMETHYLAMINO 2,2 DIMETHYLPROPYL)AMINO 1 HYDROXYMETHYLIMIDAZO[1,2 A]QUINOXALINE; 7,8 DIMETHYL 1 HYDROXYMETHYL 4 [2 (MORPHOLINO 4 YL)ETHYL]AMINOIMIDAZO[1,2 A]QUINOXALINE; 7,8 DIMETHYL 1 HYDROXYMETHYL 4 ISOBUTYLAMINOIMIDAZO[1,2 A]QUINOXALINE; 7,8 DIMETHYL 1 HYDROXYMETHYLIMIDAZO[1,2 A]QUINOXALIN 4 ONE; 7,8 DIMETHYL 4 (3 DIMETHYLAMINO 2,2 DIMETHYLPROPYL)AMINO 1 HYDROXYMETHYLIMIDAZO[1,2 A]QUINOXALINE; ADENOSINE A1 RECEPTOR ANTAGONIST; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; CATTLE; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; NONHUMAN; RADIOASSAY; RAT;

ANIMALS; BINDING, COMPETITIVE; HETEROCYCLIC COMPOUNDS; QUINOXALINES; RECEPTOR, ADENOSINE A1; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 3843073108     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.06.026     Document Type: Article

References (20)

1. S.A. Poulsen, and R.J. Quinn Bioorg. Med. Chem. 6 1998 619 641
2. S. Ceccarelli, A. D'Alessandro, M. Prinzivalli, and S. Zanarella Eur. J. Med. Chem. 33 1998 943
3. P.G. Baraldi, B. Cacciari, P.A. Borea, K. Varani, G. Pastorin, T. Da Ras, M.A. Tabrizi, F. Fruttarolo, and G. Spalluto Curr. Pharm. Des. 8 2002 2299
4. E. Novellino, E. Abignente, B. Cosimelli, G. Greco, M. Iadanza, S. Laneri, A. Lavecchia, M.G. Rimoli, F. Da Settimo, G. Primofiore, D. Tuscano, L. Trincavelli, and C. Martini J. Med. Chem. 45 2002 5030
5. V. Colotta, D. Catarzi, F. Varano, L. Cecchi, G. Filacchioni, C. Martini, L. Trincavellim, and A. Lucacchini J. Med. Chem. 43 2000 3118
6. M. Chebib, D. McKeveney, and R.J. Quinn Bioorg. Med. Chem. 8 2000 2581
7. F.D. Settimo, G. Primofiore, G. Primofiore, S. Paliani, A.M. Marini, C.L. Matta, E. Novelline, G. Grecom, A. Lucacchinim, L. Trincavelli, and C. Martini J. Med. Chem. 44 2001 316
8. F. Bondavalli, M. Botta, O. Bruno, A. Ciacci, F. Corelli, P. Fassa, A. Lucacchini, F. Manetti, C. Martini, G. Menozzi, L. Mosti, A. Ranise, S. Schenone, A. Tafi, and M.L. Trincavelli J. Med. Chem. 45 2002 4875
9. I. Doytchinova J. Comp.-Aided Mol. Des. 15 2001 29
10. S.A. Rivkees, H. Barbhaiya, and A.P. Ijzerman J. Bio. Chem. 274 1999 3617
11. W.E. Parham, and E.L. Anderson J. Am. Chem. Soc. 70 1948 4187
12. J. Ohmori, M. Shimizu-Sasamata, M. Okada, and S. Sakamoto J. Med. Chem. 40 1997 2053
13. W.C. Lumma Jr., W.C. Randall, E.L. Cresson, J.R. Hoff, R.D. Hartman, and T.F. Lyon J. Med. Chem. 26 1983 357
14. R. Ratccliffe, and R. Rodehorst J. Org. Chem. 35 1970 4000
15. A.J. Mancuso, and D. Swern Synthesis 1981 165
16. H. Vorbruggen, and K. Krolikiewicz Chem. Ber. 117 1984 1523
17. R.A. Cunha, M.D. Constantino, and J.A. Ribero Arch. Pharmacol. 359 1999 295
18. M.H. Holschbach, R. Olsson, D. Bier, W. Wutz, W. Sihver, M. Schuller, B. Palm, and H.H. Coenen J. Med. Chem. 45 2002 5150
19. M.J. Lohse, K.N. Klotz, J. Lindenborn-Fotinos, M. Reddington, U. Schwabe, and R.A. Olsson Arch. Pharmacol. 336 1987 204
20. Y.C. Cheng, and W.H. Prusoff Biochem. Pharmacol. 22 1973 3099