Syntheses and GABA receptor binding properties of 4-amino-1-, 2-, and 3- hydroxybutylphosphinic acids

Tetrahedron

Volumn 55, Issue 3, 1999, Pages 771-780

  Kehler, Jan ^a   Ebert, Bjarke ^b   Dahl, Otto ^a   Krogsgaard Larsen, Povl ^c  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b Dept of Pharmacology ^*  (Denmark)

^c UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

4 AMINO 1 HYDROXYBUTYLPHOSPHINIC ACID; 4 AMINO 2 HYDROXYBUTYLPHOSPHINIC ACID; 4 AMINO 3 HYDROXYBUTYLPHOSPHINIC ACID; 4 AMINOBUTYRIC ACID; 4 AMINOBUTYRIC ACID RECEPTOR; 4 AMINOBUTYRIC ACID RECEPTOR BLOCKING AGENT; AMINO ACID; CARBOXYLIC ACID; PHOSPHINIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BRAIN SYNAPTOSOME; GUINEA PIG; NONHUMAN; PRIORITY JOURNAL; RAT; RECEPTOR BINDING; SYNTHESIS;

ANIMALIA; CAVIA PORCELLUS; SUS SCROFA;

EID: 0033555770     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01069-2     Document Type: Article

References (26)

1. Krogsgaard-Larsen, P., Froelund, B., Kristiansen, U., Frydenvang, K., and Ebert, B. Eur.J.Pharm.Sci. 1997, 5, 355-384.
2. Froestl, W., Mickel, J. S., Sprecher, von G., Diel, P. J., Hall, R. G., Maier, L., Strub, D., Melillo, V., Baumann, P. A., Bernasconi, R., Gentsch, C., Hauser, K., Jaekel, J., Karlsson, G., Klebs, K., Maitre, L., Marescaux, C., Pozza, M. F., Schmutz, M., Steinmann, M. W., Riezen, van H., Vassout, A., Mondadori, C., Olpe, H-R., Waldmeier, P. C., and Bittiger, H. J.Med.Chem. 1995, 38, 3313-3331.
3. Froestl, W., Mickel, J. S., Hall, R. G., Sprecher, von G., Strub, D., Baumann, P. A., Brugger, F., Gentsch, C., Jaekel, J., Olpe, H-R., Rihs, G., Vassout, A., Waldmeier, P. C., and Bittiger, H. J.Med.Chem. 1995, 38, 3297-3312.
4. Kristiansen, U., Hedegaard, A., Herdeis, C., Lund, T. M., Nielsen, B., Hansen, J. J., Falch, E., Hjeds, H., and Krogsgaard-Larsen, P. J. Neurochem. 1992, 58, 1150-1159.
5. Baylis, E. K. Tetrahedron Letters 1995, 36, 9385-9388.
6. Dingwall, J. G., Ehrenfreund, J., and Hall, R. G. Tetrahedron 1989, 45, 3787-3808.
7. Petrov, K. A., Bliznyuk, N. K., Studnev, Y. N., and Kolomiets, A. F. Zhurnal Obsshc.Khim.(Engl.Transl.) 1960, 31, 168-171.
8. Sasse, K. In Houben-Weyl; Methoden der Organischen Chemie; Thieme, Stuttgart; vol.12/1, 1963, p.323.
9. Karpetsky, T. P. and White, E. H. Tetrahedron 1973, 29, 3761-3773.
10. Piper, J. R., Rose, L. M., and Johnston, T. P. J.Med.Chem. 1979, 22, 631-639.
11. Frank, W. C., Kim, Y. C., and Heck R. F. J.Org.Chem. 1978, 43, 2947-249.
12. Reddy, K. L. and Sharpless, K. B. J.Am.Chem.Soc. 1998, 120, 1207-1217.
13. O'Brien, P., Osborne, S. A. and Parker, D. D. J.Chem.Soc., Perkin Trans. I 1998, 2519-2526.
14. The Chemistry of Organophosphorus Compounds, Ed. Hartley, R., John Wiley & Sons Ltd., 1996.
15. Boyd, A. E. and Regan, A. C. Tetrahedron Letters. 1996, 35, 4223-4226.
16. Thottathil, J., Developments in the preparation and use of silicon-containing organophosphorus compounds. In, Handbook of Organophosphorus Chemistry, Ed. Engel, R., Marcel Dekker, Inc., New York, 1992, pp. 55-112.
17. Bäckvall, J-E., Oshima, K., Palermo, R. E., and Sharpless, K. B. J.Org.Chem. 1979, 44, 1953-1957.
18. Herranz, E. and Sharpless, K. B. J.Org.Chem. 1978, 43, 2544-2548.
19. Herranz, E. and Sharpless, K. B. Org.Synth. Coll. Vol. VII, 1990, 375-381.
20. Herranz, E., Biller, S. A., and Sharpless, K. B. J.Am.Chem.Soc. 1978, 100, 3596-3598.
21. Herranz, E. and Sharpless, K. B. Org.Synth. Coll. Vol. VII, 1990, 223-226.
22. Li, G., Angert, H. H., and Sharpless, K. B. Angew.Chem.Int.Ed.Engl. 1996, 35, 2813-2817.
23. Falch, E., Hedegaard, A., Nielsen, L., Jensen, B. R., Hjeds, H., and Krogsgaard-Larsen, P. J. Neurochem. 1986, 47, 898-903.
24. Kaupman, K., Huggel, K., Heid, J., Flor, P. J., Bischoff, S., Mickel, S. J., McMaster, G., Angst, C., Bittiger, H., Froestl, W., and Bettler, B. Nature 1997, 386, 239-246.
25. Wardleworth, P. S. and Baylis, E. K. Process for the Manufacture of Aliphatylphosphinic Acid Derivatives. 88810606.9 (EP0307362A2), (1988) 1-4. EU.
26. Mintz, M. J. and Walling, C. Org.Synth. Coll. Vol. V, 1983, 183-187.