Novel chiral isoxazole derivatives: Synthesis and pharmacological characterization at human β-adrenergic receptor subtypes

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 7, 2007, Pages 2533-2543

  Dallanoce, Clelia ^a   Frigerio, Fabio ^a   De Amici, Marco ^a   Dorsch, Sandra ^b   Klotz, Karl Norbert ^b   De Micheli, Carlo ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Binding affinity; Efficacy; Human adrenergic receptor subtypes; Hybrid compounds; Isoxazole derivatives; Synthesis

Indexed keywords

1 (3 BROMOISOXAZOL 5 YL) 2 [[2 (4 BUTOXYPHENYL) 1 METHYLETHYL]AMINO]ETHANOL; 4 [2 [[2 (3 CHLOROPHENYL) 2 HYDROXYETHYL]AMINO]PROPYL]PHENOXYACETIC ACID; 4 [2 [[[2 (3 BROMOISOXAZOL 5 YL) 2 HYDROXYETHYL]AMINO]PROPYL]PHENOXY]ACETIC ACID; BETA ADRENERGIC RECEPTOR; BROXATEROL; ETHYL [4 [2 [[2 (3 BROMOISOXAZOL 5 YL) 2 HYDROXYETHYL]AMINO]PROPYL]PHENOXY]ACETATE; ISOXAZOLE DERIVATIVE; PARTIAL AGONIST; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BRONCHODILATING ACTIVITY; CHIRALITY; CHO CELL; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DETERMINATION; DRUG EFFICACY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ISOMERIZATION; NONHUMAN; RECEPTOR AFFINITY; STEREOISOMERISM;

ADENYLATE CYCLASE; ANIMALS; CELL MEMBRANE; CHO CELLS; CRICETINAE; CRICETULUS; HUMANS; INDICATORS AND REAGENTS; ISOXAZOLES; MAGNETIC RESONANCE SPECTROSCOPY; RADIOLIGAND ASSAY; RECEPTORS, ADRENERGIC, BETA-2; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

CRICETULUS GRISEUS;

EID: 33847627129     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.01.056     Document Type: Article

References (40)

1. McGraw D.W., and Liggett S.B. Proc. Am. Thorac. Soc. 2 (2005) 292
2. Johnson M. J. Allergy Clin. Immunol. 117 (2006) 18
3. Satwani S., Dec G.W., and Narula J. J. Cardiovasc. Pharmacol. Therapeut. 9 (2004) 243
4. Wallukat G. Herz 27 (2002) 683
5. Nicholas A.P., Hökfelt T., and Pieribone V. Trends Pharmacol. Sci. 17 (1996) 245
6. Frielle T., Collins S., Daniel K.W., Caron M.G., Lefkowitz R.J., and Kobilka B.K. Proc. Natl. Acad. Sci. U.S.A. 84 (1987) 7920
7. Dixon R.A., Kobilka B.K., Strader D.J., Benovic J.L., Dohlman H.G., and Frielle T. Nature 321 (1986) 75
8. Emorine L.J., Marullo S., Briend-Sutren M.M., Patey G., Tate K., Delavier-Klutchko C., and Strosberg A.D. Science 245 (1989) 1118
9. Hall R.A. Semin. Cell Dev. Biol. 15 (2004) 281 and references cited therein
10. Poole-Wilson P.A., Swedberg K., Cleland J.G.F., Di Lenarda A., Hanrath P., Komajda M., Lubsen J., Lutiger B., Metra M., Remme W.J., Torp-Pedersen C., Scherhag A., and Skene A. Lancet 362 (2003) 7
11. Silverman E.S., Liggett S.B., Gelfand E.W., Rosenwasser L.J., Baron R.M., Bolk S., Weiss S.T., and Drazen J.M. Pharmacogenomics J. 1 (2001) 27 and references cited therein
12. Robidoux J., Martin T.L., and Collins S. Annu. Rev. Pharmacol. Toxicol. 44 (2004) 297 and references cited therein
13. Tanaka N., Tamai T., Mukaiyama H., Hirabayashi A., Muranaka H., Ishikawa T., Kobayashi J., Akahane S., and Akahane M. J. Med. Chem. 46 (2003) 105
14. Furse K.E., and Lybrand T.P. J. Med. Chem. 46 (2003) 4450 and references cited therein
15. Baker J.G., Hall I.P., and Hill S.J. Mol. Pharmacol. 63 (2003) 1312
16. Alves I.D., Cowell S.M., Salamon Z., Devanathan S., Tollin G., and Hruby V.J. Mol. Pharmacol. 65 (2004) 1248
17. Kobilka B. Mol. Pharmacol. 65 (2004) 1060
18. Conti P., Dallanoce C., De Amici M., De Micheli C., and Klotz K.-N. Bioorg. Med. Chem. 6 (1998) 401
19. De Amici M., Conti P., Dallanoce C., Kassi L., Castellano S., Stefancich G., and De Micheli C. Med. Chem. Res. 10 (2000) 69
20. Dallanoce C., Meroni G., De Amici M., Hoffmann C., Klotz K.-N., and De Micheli C. Bioorg. Med. Chem. 14 (2006) 4393
21. Sala R., Moriggi E., Della Bella D., and Carenzi A. Eur. J. Pharmacol. 203 (1991) 17
22. Drug Future 16 (1991) 163
23. Drug Future 17 (1992) 136
24. Drug Future 18 (1993) 162
25. Hoffmann C., Leitz M.R., Oberdorf-Maass S., Lohse M.J., and Klotz K.-N. Naunyn-Schmiedeberg's Arch. Pharmacol. 369 (2004) 151
26. De Amici M., De Micheli C., Carrea G., and Spezia S. J. Org. Chem. 54 (1989) 2646
27. Larsen A.A., Gould W.A., Roth H.R., Comer W.T., Uloth R.H., and Dungan K. J. Med. Chem. 10 (1967) 462
28. Sum F.-W., Wong V., Han S., Largis E., Mulvey R., and Tillet J. Bioorg. Med. Chem. Lett. 13 (2003) 2191
29. Arch J.R.S., Ainsworth A.T., Cawthorne M.A., Piercy V., Sennitt M.V., Thody V.E., Wilson C., and Wilson S. Nature 309 (1984) 163
30. Uehling D.E., Shearer B.G., Donaldson K.H., Chao E.Y., Deaton D.N., Adkinson K.K., Brown K.K., Cariello N.F., Faison W.L., Lancaster M.E., Lin J., Hart R., Milliken T.O., Paulik M.A., Sherman B.W., Sugg E.E., and Cowan C. J. Med. Chem. 49 (2006) 2758
31. Lepage, F.; Hublot, B.; Adolphe, P.S. FR 2750425-A1, 1996.
32. Nahm S., and Weinreb S.M. Tetrahedron Lett. 22 (1981) 3815
33. Singh J., Satyamurthi N., and Aidhen I.S. J. Prakt. Chem. 342 (2000) 340
34. Williams J.M., Jobson R.B., Yasuda N., Marchesini G., Dolling U.-H., and Grabowski E.J.J. Tetrahedron Lett. 36 (1995) 5461
35. Kohno H., Iwakuma T., and Yamada K. Synth. Comm. 28 (1998) 1935
36. Bloom J.D., Dutia M.D., Johnson B.D., Wissner A., Burns M.G., Largis E.E., Dolan J.A., and Claus T.H. J. Med. Chem. 35 (1992) 3081
37. Capanec I., Litvić M., Mikuldaš H., Bartolinčic V., and Vinković V. Tetrahedron 59 (2003) 2435
38. Behr B., Hoffmann C., Ottolina G., and Klotz K.-N. J. Biol. Chem. 281 (2006) 18120
39. Klotz K.-N., Hessling J., Hegler J., Owman C., Kull B., Fredholm B.B., and Lohse M.J. Naunyn-Schmiedeberg's Arch. Pharmacol. 357 (1998) 1
40. De Lean A., Hancock A.A., and Lefkowitz R.J. Mol. Pharmacol. 21 (1982) 5