Synthesis and β-adrenoceptor agonist properties of (±)-1-(3',4'- dihydroxyphenoxy)-3-(3',4'-dimethoxyphenyl) ethylamino-2-propanol hydrochloride, (±)-RO363.HCl, and the (2S)-(-)-isomer

European Journal of Medicinal Chemistry

Volumn 34, Issue 6, 1999, Pages 539-548

  Iakovidis, Dimitri ^a   Louis, Simon N S ^a   Rezmann, Linda A ^a   Colagrande, Felicia ^a   Nero, Tracy L ^a   Jackman, Graham P ^a   Louis, William J ^a  

^a UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

(2S) ( ) RO363; ( ) RO363; Chiral synthesis; CHO cells; 1 adrenoceptor agonist

Indexed keywords

1 (3,4 DIHYDROXYPHENOXY) 3 (3,4 DIMETHOXYPHENETHYLAMINO) 2 PROPANOL; BETA 1 ADRENERGIC RECEPTOR; BETA 2 ADRENERGIC RECEPTOR;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CHIRALITY; CHO CELL; ENANTIOMER; NONHUMAN; RACEMIC MIXTURE; SYNTHESIS;

EID: 0032758313     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(99)80103-2     Document Type: Article

References (26)

1. Raper C., McPherson G.A., Iakovidis D. Eur. J. Pharmacol. 52:1978;241-242.
2. Iakovidis D., Malta E., McPherson G.A., Raper C. Br. J. Pharmacol. 68:1980;677-685.
3. McPherson G.A., Malta E., Molenaar P., Raper C. Br. J. Pharmacol. 82:1984;897-904.
4. Molenaar P., Sarsero D., Arch J.R.S., Kelly J., Henson S.M., Kaumann A.J. Br. J. Pharmacol. 120:1997;165-176.
5. Molenaar P., Sarsero D., Kaumann A.J. Clin. Exp. Pharmacol. Physiol. 24:1997;647-656.
6. Iakovidis D., Structure Activity Relationships in Medicinal Chemistry, Ph D Thesis Deakin University, Victoria, Australia, 1984.
7. Godfrey I.M., Sargent M.V., Elix J.A. J. Chem. Soc. Perkin Trans. I:1974;1353-1354.
8. Klunder J.M., Onami T., Sharpless K.B. J. Org. Chem. 54:1989;1295-1304.
9. Bryan L.J., Cole J.J., O'Donnell S.R., Wanstall J.C. J. Pharmacol. Exp. Ther. 216 (2):1981;395-400.
10. Dyke A., Anugs J.A. J. Auton. Pharmacol. 8 (3):1988;219-228.
11. Goodman A.G., Goodman L.S., Rall T.W., Murad F. The Pharmacological Basis of Therapeutics. 1985;Macmillan Publishing Company, NY, USA.
12. Malta E., McPherson A.G., Raper C. TIPS Reviews. 1985;400-403.
13. Hieble J.P. Ruffolo R.R Jr. β-Adrenoceptors: Molecular Biology, Biochemistry and Pharmacology. Prog. Basic Clin. Pharmacol., vol. 7. 1991;105-172 Karger, Basel.
14. Snow H.M. Br. J. Clin. Pharmacol. 28:1989;3S-13S.
15. Maccarrone C., Malta E., Raper C. J. Cardiovasc. Pharmacol. 6:1984;132-141.
16. Wenke M., Trcka V., Blaha L., Hodrova J., Weichet M., Czech., 131 (1969) 157 in: Chem. Abstr. 72 (1970) 111007.
17. Wenke M., Trcka V., Blaha L., Hodrova J., Weichet M., Czech., 131 (1969) 157 in: Chem. Abstr. 72 (1970) 111007.
18. Ablad B., Brogard M., Corrodi H. Acta Pharm. Suesica. 7:1970;551-558.
19. Casagrande C., Ferrini R., Miragoli G., Ferrari G. Boll. Chim. Farm. 112:1973;445-454.
20. Tung L., Jackman G., Campbell B., Louis S., Iakovidis D., Louis W.J. J. Cardiovasc. Pharmacol. 21:1993;484-488.
21. Blin N., Camoin L., Maigret B., Strosberg A.D. Mol. Pharmacol. 44:1993;1094-1104.
22. Gros J., Manning B.S., Pietri-Rouxel F., Guillaume J.L., Drumare M.F., Strosberg A.D. Eur. J. Biochem. 251:1998;590-596.
23. Zaborowsky B.R., McMahan W.C., Griffin W.A., Norris F.H., Ruffolo R.R. Jr.,. J. Pharmacol. Methods. 4:1980;165-178.
24. Van Rossum J.M., Hurkmans J.A.T.H.M., Wolters C.J.J. Arch. Int. Pharmacodyn. Therap. 143:1963;299-330.
25. McPherson G.A. Comput. Programs Biom. 17:1983;107-113.
26. Munson P.J., Rodbard D. Anal. Biochem. 109:1980;220-239.