Design and synthesis of novel imidazo[1,2-a]quinoxalines as PDE4 inhibitors

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 5, 2004, Pages 1129-1139

  Deleuze Masquéfa, Carine ^a   Gerebtzoff, Grégori ^a   Subra, Guy ^a   Fabreguettes, Jean Roch ^a   Ovens, Annabel ^a   Carraz, Maëlle ^a   Strub, Marie Paule ^b   Bompart, Jacques ^a   George, Pascal ^c   Bonnet, Pierre Antoine ^a  

^a Laboratoire de Pharmacochimie   (France)

^b CENTRE DE BIOCHIMIE STRUCTURALE   (France)

^c SANOFI   (France)

Author keywords

Imidazo 1,2 a quinoxaline; Phosphodiesterase 4; Phosphodiesterase inhibition

Indexed keywords

(1 ISOBUTYL 4 PIPERAZIN 1 YL)IMIDAZO[1,2 A]QUINOXALINE; (1 ISOBUTYL 4 PIPERIDIN 1 YL)IMIDAZO[1,2 A]QUINOXALINE; (1 ISOBUTYL 4 PYRROLIDIN 1 YL)IMIDAZO[1,2 A]QUINOXALINE; 1 (2 PHENYLETHYL) IMIDAZO[1,2 A]QUINOXALINE 4(5H) ONE; 1 ISOBUTYL N (2 METHOXYETHYL)IMIDAZO[1,2 A]QUINOXALIN 4 AMINE; 1 ISOBUTYL N (2 PHENYLETHYL)IMIDAZO[1,2 A]QUINOXALIN 4 AMINE; 1 ISOBUTYL N BENZYLIMIDAZO[1,2 A]QUINOXALIN 4 AMINE; 1 ISOBUTYL N METHYLIMIDAZO[1,2 A]QUINOXALIN 4 AMINE; 1 ISOBUTYL N PHENYLIMIDAZO[1,2 A]QUINOXALIN 4 AMINE; 1 ISOBUTYL N,N DIMETHYLIMIDAZO[1,2 A]QUINOXALINE 4 AMINE; 1 ISOBUTYLIMIDAZO[1,2 A]QUINOXALINE 4 AMINE; 1 ISOBUTYLIMIDAZO[1,2 A]QUINOXALINE 4(5H) ONE; 1 [(3 CHLOROQUINOXALIN 2 YL)AMINO] 4 METHYLPENTAN 2 OL; 1 [(3 CHLOROQUINOXALIN 2 YL)AMINO] 4 METHYLPENTAN 2 ONE; 1 [(3 CHLOROQUINOXALIN 2 YL)AMINO] 4 PHENYLBUTAN 2 OL; 1 [(3 CHLOROQUINOXALIN 2 YL)AMINO] 4 PHENYLBUTAN 2 ONE; 4 CHLORO 1 (2 PHENYLETHYL)IMIDAZO[1,2 A]QUINOXALINE; 4 CHLORO 1 ISOBUTYLIMIDAZO[1,2 A]QUINOXALINE; N METHYL 1 (2 PHENYLETHYL)IMIDAZO[1,2 A]QUINOXALINE 4 AMINE; N PHENYL 1 (2 PHENYLETHYL)IMIDAZO[1,2 A]QUINOXALIN 4 AMINE; N,1 BIS(2 PHENYLETHYL)IMIDAZO[1,2 A]QUINOXALIN 4 AMINE; N,N DIMETHYL 1 (2 PHENYLETHYL)IMIDAZO[1,2 A]QUINOXALINE 4 AMINE; PHOSPHODIESTERASE IV INHIBITOR; QUINOXALINE DERIVATIVE; TERT BUTYL 4 (1 ISOBUTYLIMIDAZO[1,2 A]QUINOXALIN 4 YL)PIPERAZINE 1 CARBOXYLATE; TERT BUTYL 4 [1 (2 PHENYLETHYL)IMIDAZO[1,2 A]QUINOXALIN 4 YL]PIPERAZINE 1 CARBOXYLATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; [1 (2 PHENYLETHYL) 4 PIPERIDIN 1 YL]IMIDAZO[1,2 A]QUINOXALINE; [1 (2 PHENYLETHYL) 4 PYRROLIDIN 1 YL]IMIDAZO[1,2 A]QUINOXALINE;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; DRUG POTENCY; DRUG SYNTHESIS; EPITHELIUM CELL; HUMAN; HUMAN CELL; MOLECULAR DYNAMICS; POLYMERIZATION;

EID: 10744230294     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2003.11.034     Document Type: Article

References (17)

1. Dal Piaz V., Giovannoni M.P. Eur. J. Med. Chem. 35:2000;463.
2. Soderling S.H., Bayuga S.J., Beavo J.A. Proc. Natl. Acad. Sci. U.S.A. 95:1998;8991.
3. Conti M., Richter W., Mehats C., Livera G., Park J.Y., Jin C. J. Biol. Chem. 278:2003;5493.
4. Houslay M.D., Adams D.R. Biochem. J. 370:2003;1.
5. Souness J.E., Aldous D., Sargent C. Immunopharmacology. 47:2000;127.
6. Wright L.C., Seybold J., Robichaud A., Adcock I.M., Barnes P.J. Am. J. Physiol. 275:1998;L694.
7. Burnouf C., Pruniaux M.P. Curr. Pharm. Des. 8:2002;1255.
8. Sturton G., Fitzgerald M. Chest. 121:2002;192S.
9. Parra S., Laurent F., Subra G., Deleuze-Masquéfa C., Benezech V., Fabreguettes J., Vidal J., Pocock T., Elliott K., Small R., Escale R., Michel A., Chapat J., Bonnet P. Eur. J. Med. Chem. 36:2001;255.
10. Lumma W.C. Jr., Randall W.C., Cresson E.L., Huff J.R., Hartman R.D., Lyon T.F. J. Med. Chem. 26:1983;357.
11. Meurer L.C., Tolman R.L., Chapin E.W., Saperstein R., Vicario P.P., Zrada M.M., MacCoss M. J. Med. Chem. 35:1992;3845.
12. Dent G., White S.R., Tenor H., Bodtke K., Schudt C., Leff A.R., Magnussen H., Rabe K.F. Pulm. Pharmacol. Ther. 11:1998;47.
13. Mehats C., Andersen C.B., Filopanti M., Jin S.L., Conti M. Trends Endocrinol. Metab. 13:2002;29.
14. Souness J.E., Rao S. Cell Signal. 9:1997;227.
15. Vitse O., Laurent F., Pocock T.M., Benezech V., Zanik L., Elliott K.R., Subra G., Portet K., Bompart J., Chapat J.P., Small R.C., Michel A., Bonnet P.A. Bioorg. Med. Chem. 7:1999;1059.
16. Schelhaas M., Waldmann H. Angew. Chem., Int. Ed. Engl. 35:1996;2056.
17. Klee C.B. Biochemistry. 16:1977;1017.