Synthesis and β-blocking activity of (R,S)-(E)-oximeethers of 2,3-dihydro-1,8-naphthyridine and 2,3-dihydrothiopyrano[2,3-b]pyridine: Identification of β3-antagonists

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 23, 2003, Pages 4921-4931

  Saccomanni, Giuseppe ^a   Badawneh, Muwaffag ^b   Adinolfi, Barbara ^a   Calderone, Vincenzo ^a   Cavallini, Tiziana ^a   Ferrarini, Pier Luigi ^a   Greco, Rosamiria ^a   Manera, Clementina ^a   Testai, Lara ^a  

^a UNIVERSITY OF PISA   (Italy)

^b THOMAS JEFFERSON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4(1H) [1 (3 ISOPROPYLAMINO 2 HYDROXYPROPYL)OXYIMINO] 2,3 DIHYDRO 1,8 NAPHTHYRIDINE; 4(1H) [1 (3 ISOPROPYLAMINO 2 HYDROXYPROPYL)OXYIMINO] 6 BROMO 1,7 DIMETHYL 2,3 DIHYDRO 1,8 NAPHTHYRIDINE; 4(1H) [1 (3 ISOPROPYLAMINO 2 HYDROXYPROPYL)OXYIMINO] 6 BROMO 2,3 DIHYDRO 1,8 NAPHTHYRIDINE; 4(1H) [1 (3 ISOPROPYLAMINO 2 HYDROXYPROPYL)OXYIMINO] 7 (4 CHLOROPHENOXY) 2,3 DIHYDRO 1,8 NAPHTHYRIDINE; 4(1H) [1 (3 ISOPROPYLAMINO 2 HYDROXYPROPYL)OXYIMINO] 7 (4 TERT BUTYLPHENOXY) 2,3 DIHYDRO 1,8 NAPHTHYRIDINE; 4(1H) [1 (3 ISOPROPYLAMINO 2 HYDROXYPROPYL)OXYIMINO] 7 PHENOXY 2,3 DIHYDRO 1,8 NAPHTHYRIDINE; 4(1H) [1 (3 TERT BUTYLAMINO 2 HYDROXYPROPYL)OXYIMINO] 2,3 DIHYDRO 1,8 NAPHTHYRIDINE; 4(1H) [1 (3 TERT BUTYLAMINO 2 HYDROXYPROPYL)OXYIMINO] 6 BROMO 1,7 DIMETHYL 2,3 DIHYDRO 1,8 NAPHTHYRIDINE; 4(1H) [1 (3 TERT BUTYLAMINO 2 HYDROXYPROPYL)OXYIMINO] 6 BROMO 2,3 DIHYDRO 1,8 NAPHTHYRIDINE; 4(1H) [1 (3 TERT BUTYLAMINO 2 HYDROXYPROPYL)OXYIMINO] 7 (4 CHLOROPHENOXY) 2,3 DIHYDRO 1,8 NAPHTHYRIDINE; 4(1H) [1 (3 TERT BUTYLAMINO 2 HYDROXYPROPYL)OXYIMINO] 7 (4 TERT BUTYLPHENOXY) 2,3 DIHYDRO 1,8 NAPTHYRIDINE; 4(1H) [1 (3 TERT BUTYLAMINO 2 HYDROXYPROPYL)OXYIMINO] 7 PHENOXY 2,3 DIHYDRO 1,8 NAPHTHYRIDINE; 4(4H) [1 (3 ISOPROPYLAMINO 2 HYDROXYPROPYL)OXYIMINO] 2,3 DIHYDROTHIOPYRANO[2,3 B]PYRIDINE; 4(4H) [1 (3 TERT BUTYLAMINO 2 HYDROXYPROPYL)OXYIMINO] 2,3 DIHYDROTHIOPYRANO[2,3 B]PYRIDINE; BETA 3 ADRENERGIC RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BETA ADRENERGIC RECEPTOR BLOCKING; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; MALE; NONHUMAN; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

EID: 0242298238     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2003.09.017     Document Type: Article

References (40)

1. Hoffman, B.B.; Lefkowitz, R. J. In The Pharmacological Basis of Therapeutics, 9th ed.; Hardman, J. G., Goodman Gilman, A., Limbird, L. E., Eds. ; McGraw-Hill: New York, 1995; p 232.
2. Blanc M., Tamir A., Aubriot S., Michel M.C., Bouzoubaa M., Leclerc G., Demenge P. J. Med. Chem. 41:1998;1613.
3. Leclerc G., Mann A., Wermuth C.G. J. Med. Chem. 20:1977;1657.
4. Fravolini A., Schiaffella F., Orzalesi G., Selleri R., Volpato I. Eur. J. Med. Chem. 13:1978;347.
5. Martani A., Magli M., Orzalesi G., Selleri R. Farmaco Ed. Sci. 30:1975;370.
6. Baldwin J.J., McClure D.E., Gross D.M., Williams M. J. Med. Chem. 25:1982;931.
7. Amlaiky N., Leclerc G., Decker N., Schwartz J. Eur. J. Med. Chem. 19:1984;341.
8. Rakhit S., Bouzoubaa M., Leclerc G., Leger J.M., Carpy A. Eur. J. Med. Chem. 21:1986;411.
9. Jamart-Gregoire B., Caubere P., Blanc M., Gnassounou J.P., Advenier C. J. Med. Chem. 32:1989;315.
10. Ferrarini P.L., Mori C., Primofiore G., Da Settimo A., Breschi M.C., Martinotti E., Nieri P., Ciucci M.A. Eur. J. Med. Chem. 25:1990;489.
11. Ferrarini P.L., Mori C., Badawneh M., Manera C., Saccomanni G., Calderone V., Scatizzi R., Barili P.L. Eur. J. Med. Chem. 32:1997;955.
12. Ferrarini P.L., Mori C., Badawneh M., Calderone V., Greco R., Manera C., Martinelli A., Nieri P., Saccomanni G. Eur. J. Med. Chem. 35:2000;815.
13. Balsamo A., Breschi M.C., Chini M., Domiano P., Giannaccini G., Lucacchini A., Macchia B., Macchia M., Manera C., Martinelli A., Martini C., Martinotti E., Nieri P., Rossello A. Eur. J. Med. Chem. 27:1992;751.
14. Macchia B., Balsamo A., Breschi M.C., Chiellini G., Macchia M., Martinelli A., Martini C., Nardini C., Nencetti S., Rossello A., Scatizzi R. J. Med. Chem. 37:1994;1518.
15. Balsamo A., Gentili D., Lapucci A., Macchia M., Martinelli A., Orlandini E. Farmaco. 49:1994;759.
16. Balsamo A., Lapucci A., Macchia B., Macchia M., Orlandini E., Rossello A. Farmaco. 50:1995;239.
17. Gentili D., Lapucci A., Macchia B., Macchia M., Martinelli A., Nencetti S., Orlandini E., Ferni G., Pinza M. Farmaco. 50:1995;519.
18. Bouzoubaa M., Leclerc G., Decker N., Schwartz J., Andermann G. J. Med. Chem. 27:1984;1291.
19. Macchia B., Balsamo A., Lapucci A., Macchia F., Breschi M.C., Fantoni B., Martinotti E. J. Med. Chem. 28:1985;153.
20. Bouzoubaa M., Leclerc G., Rakhit S., Andermann G. J. Med. Chem. 28:1985;896.
21. Himber J., Sallee V., Andermann G., Bouzoubaa M., Leclerc G., De Santis L. J. Ocul. Pharmacol. 3:1987;111.
22. Arch J.R.S., Ainsworth A.T., Ellis R.D.M., Piercy V., Thody V.E., Thurlby P.L., Wilson C., Wilson S., Young P. J. Obes. 8(Suppl. 1):1984;1.
23. Meier M.K., Alig L., Burgi-Saville M.E., Muller M. J. Obes. 8(Suppl. 1):1984;215.
24. Yen T.T., McKee M.M., Stamm N.B. J. Obes. 8(Suppl. 1):1984;65.
25. Cawthorne M.A., Carroll M.J., Levy A.L., Lister C.L., Sennitt M.V., Smith S.A., Young P. J. Obes. 8(Suppl. 1):1984;93.
26. Emorine L.J., Marullo S., Briend-Sutren M.-M., Patey G., Tate T., Delavier-Klutchko C., Strosberg A.D. Science. 245:1989;1118.
27. Arch J.R.S., Ainsworth A.T. J. Obes. 7:1983;85.
28. Arch J.R.S., Ainsworth A.T., Cawthorne M.A., Piercy V., Sennitt M.V., Thody V.E., Wilson C., Wilson S. Nature. 309:1984;163.
29. Gauthier C., Langin D., Balligand J.L. Trends Pharmacol. Sci. 21:2000;426.
30. Zulet M.A., Berraondo B., Milagro F.I., Martinez J.A. Farmaco. 54:1999;710.
31. He J., Nikulin I., Vansal S.S., Feller D.R., Miller D.D. J. Med. Chem. 43:2000;591.
32. Tanaka N., Tamai T., Mukaiyama H., Hirabayshi A., Muranaka H., Akahane S., Miyata H., Akahane M. J. Med. Chem. 44:2001;1436.
33. Da Settimo A., Biagi G., Primofiore G., Ferrarini P.L., Livi O. Farmaco Ed. Sci. 33:1978;770.
34. Da Settimo A., Marini A.M., Primofiore G., Da Settimo F., La Motta C., Pardi G., Ferrarini P.L., Mori C. J. Heterocyclic Chem. 37:1999;379.
35. Candelore M.R., Deng L., Tota L., Guan X.-M., Amend A., Liu Y., Newbold R., Cascieri M.A., Weber A.E. J. Pharmacol. Exp. Ther. 290:1999;649.
36. Rodbell M. J. Biol. Chem. 239:1964;375.
37. Cushman S. J. Cell Biol. 46:1970;326.
38. Wieland O. Biochem. Z. 239:1957;313.
39. Calderone V.J. Pharmacol. Toxicol. Methods. 39:1998;129.
40. Gaddum J.H. Pharmacol. Rev. 9:1957;211.