Structure-lipophilicity relationships of neutral and protonated β- blockers. Part I. Intra- and intermolecular effects in isotropic solvent systems

Helvetica Chimica Acta

Volumn 82, Issue 8, 1999, Pages 1211-1222

  Caron, Giulia ^a   Steyaert, Guillaume ^a   Pagliara, Alessandra ^a   Reymond, Frédéric ^b   Crivori, Patrizia ^a   Gaillard, Patrick ^a   Carrupt, Pierre Alain ^a   Avdeef, Alex ^b   Comer, John ^c   Box, Karl J ^d   Girault, Hubert H ^b   Testa, Bernard ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

^b EPFL   (Switzerland)

^c PION INC   (United States)

^d Sirius Analytical Instruments Ltd   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 DICHLOROETHANE; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; ETHER DERIVATIVE; OCTANOL; WATER;

ARTICLE; CYCLIC POTENTIOMETRY; DRUG STRUCTURE; LIPOPHILICITY; MOLECULAR INTERACTION; PARTITION CHROMATOGRAPHY; TITRIMETRY; VALIDATION PROCESS;

EID: 0032814354     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1522-2675(19990804)82:8<1211::AID-HLCA1211>3.0.CO;2-K     Document Type: Article

References (33)

1. B.G. Main, H. Tucker, in 'Progress in Medicinal Chemistry, Vol 22', Elsevier Science Publishers, 1985, pp. 121-164.
2. B. G. Main, H. Tucker, in 'Medicinal Chemistry', Eds. C. R. Ganellin and S. M. Roberts, Academic Press, London, 1993, Vol. 4, pp. 187-208.
3. S. Ferrari, T. Leemann, P. Dayer, Life Sci. 1991, 48, 2259.
4. D. E. Drayer, Pharmacotherapy 1987, 7, 87.
5. G. Cheymol, J. M. Poirier, J. Barré, A. Pradalier, J. Dry, J. Clin. Pharmacol. 1987, 27, 874.
6. I. Kobayashi, K. Hosaka, T. Ueno, H. Maruo, M. Kamiyama, C. Konno, M. Gemba, Biol. Pharm. Bull. 1997, 20, 421.
7. Y. Yamada, K. Ito, K. Nakamura, Y. Sawada, T. Iga, Biol. Pharm. Bull. 1993, 16, 1251.
8. R. Fruttero, G. Caron, E. Fornatto, D. Boschi, G. Ermondi, A. Gasco, P. A. Carrupt, B. Testa, Pharm. Res. 1998, 15, 1407.
9. F. Barbato, M. I. La Rotonda, F. Quaglia, Eur. J. Med. Chem. 1996, 31, 311.
10. A. Avdeef, K. J. Box, J. E. A. Comer, C. Hibbert, K. Y. Tam, Pharm. Res. 1998, 15, 209.
11. G. Caron, P. Gaillard, P. A. Carrupt, B. Testa, Helv. Chim. Acta 1997, 80, 449.
12. G. Steyaert, G. Lisa, P. Gaillard, G. Boss, F. Reymond, H. H. Girault, P. A. Carrupt, B. Testa, J. Chem. Soc., Faraday Trans. 1997, 93, 401.
13. A. Pagliara, G. Caron, G. Lisa, W. Fan, P. Gaillard, P. A. Carrupt, B. Testa, M. H. Abraham, J. Chem. Soc., Perkin Trans. 2 1997, 2639.
14. R. S. Tsai, P. A. Carrupt, B. Testa, in 'ACS Symposium Series 593. Modern Contercurrent Chromatography', Eds. W. D. Conway and P. J. Petroski, American Chemical Society, Washington DC, 1995, pp. 143-154.
15. A. Avdeef, in 'Lipophilicity in Drug Action and Toxicology', Eds. V. Pliska, B. Testa, and H. van de Waterbeemd, VCH Publishers, Weinheim, 1996, pp. 109-139.
16. F. Reymond, G. Steyaert, P. A. Carrupt, B. Testa, H. H. Girault, Helv. Chim. Acta 1996, 79, 101.
17. Medchem95 database. Daylight Chemical Information System, Inc., Irvine, California, 1995.
18. P. A. Carrupt, B. Testa, P. Gaillard, in 'Reviews in Computational Chemistry', Eds. D. B. Boyd and K. B. Lipkowitz. Wiley-VCH, New York, 1997, Vol. 11, pp. 241-315.
19. CLIP1.0. Institute of Medicinal Chemistry, University of Lausanne, 1996.
20. F. Reymond, P. A. Carrupt, B. Testa, H. H. Girault, Chem. Eur. J. 1999, 5, 39.
21. R. C. Young, C. R. Ganellin, R. Griffiths, R. C. Mitchell, M. E. Parsons, D. Saunders, N. E. Sore, Eur. J. Med. Chem. 1993, 28, 201.
22. R. C. Young, R. C. Mitchell, T. H. Brown, C. R. Ganellin, R. Griffiths, M. Jones, K. K. Rana, D. Saunders, I. R. Smith, N. E. Sore, T. J. Wilks, J. Med. Chem. 1988, 31, 656.
23. R. Schoenwald, H. S. Huang, J. Pharm. Sci. 1983, 72, 1266.
24. M. H. Abraham, H. S. Chadha, in 'Lipophilicity in Drug Action and Toxicology', Eds. V. Pliska, B. Testa and H. van de Waterbeemd, VCH Publishers, Weinheim, 1996, pp. 311-337.
25. A. Avdeef, Quant. Struct.-Act. Relat. 1992, 11, 510.
26. A. Avdeef, J. E. A. Comer, S. J. Thomson, Anal. Chem. 1993, 65, 42.
27. K. Takacs-Novak, A. Avdeef, J. Pharm. Biomed. Anal. 1996, 14, 1405.
28. F. Reymond, G. Steyaert, P. A. Carrupt, B. Testa, H. H. Girault, J. Am. Chem. Soc. 1996, 118, 11951.
29. F. Reymond, P. F. Brevet, P. A. Carrupt, H. H. Girault, J. Electroanal. Chem. 1997, 424, 121.
30. 1,2-Dichloroethane (Environmental Health Criteria No 176), World Health Organization, Geneva, 1995.
31. N. El Tayar, R. S. Tsai, P. Vallat, C. Altomare, B. Testa, J. Chromatogr. 1991, 556, 181.
32. SYBYL 6.2. Tripos Associates, Inc., St-Louis, Missouri, 1995.
33. J. C. Dearden, Environ. Health Perspect. 1985, 61, 203.