New substrates and inhibitors of γ-aminobutyric acid aminotransferase containing bioisosteres of the carboxylic acid group: Design, synthesis, and biological activity

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 5, 2006, Pages 1331-1338

  Yuan, Hai ^a   Silverman, Richard B ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

Bioisostere; GABA AT; Tetrazole; Vigabatrin

Indexed keywords

1H TETRAZOLE 5 (ALPHA VINYLPROPANAMINE); 1H TETRAZOLE 5 ETHANAMINE; 4 AMINOBUTYRATE AMINOTRANSFERASE; 4 AMINOBUTYRATE AMINOTRANSFERASE INHIBITOR; CARBAMIC ACID DERIVATIVE; INDOLE 5 METHANAMINE; INDOLE DERIVATIVE; LIGAND; METHYL BETA ALANYLCARBAMATE; METHYL BETA ALANYLSULFONAMIDE; METHYLAMINE; SULFONAMIDE; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; DRUG COMPARISON; DRUG DESIGN; DRUG INHIBITION; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; ENZYME SUBSTRATE; METHYLATION;

4-AMINOBUTYRATE TRANSAMINASE; ANTICONVULSANTS; BINDING SITES; CARBOXYLIC ACIDS; ENZYME INHIBITORS; GAMMA-AMINOBUTYRIC ACID; KINETICS; MODELS, CHEMICAL; TETRAZOLES; VIGABATRIN;

EID: 31044440811     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.09.067     Document Type: Article

References (30)

1. A. Cooper J. Methods Enzymol. 113 1985 80 82
2. K. Krnjevic Physiol. Rev. 54 1974 418 505
3. O. Hornykiewicz, K.B. Lloyd, and L. Davidson E. Roberts T.N. Chase D.B. Tower GABA in Nervous System Function 1976 Raven Press New York 479 485
4. T.L. Perry, S. Hansen, and M. Kloster New Engl. J. Med. 288 1973 337 342
5. T. Aoyage, T. Wada, M. Nagai, F. Kojima, S. Harada, T. Takeuchi, H. Takahashi, K. Kirokawa, and T. Tsumita Chem. Pharm. Bull. 38 1990 1748 1749
6. K. Gale Epilepsia 30 1989 1 11
7. A. Karlsson, F. Funnum, D. Malthe-Sorrensen, and J. Storm-Mathisen Biochem Pharmacol 22 1974 3053 3061
8. D.P. Purpura, M. Girando, T.A. Smith, D.A. Callan, and J. Groundfest J. Neurochem. 3 1959 238 268
9. D.B. Tower E. Roberts T.N. Chase D.B. Tower GABA in Nervous System Function 1976 Raven Press New York 461 478
10. S.M. Nanavati, and R.B. Silverman J. Med. Chem. 32 1989 2413 2421
11. B. Lippert, B.W. Metcalf, M.J. Jung, and P. Casara Eur. J. Biochem. 74 1977 441 445
12. Y. Pan, J. Qiu, and R.B. Silverman J. Med. Chem. 46 2003 5292 5293
13. S. Choi, and R.B. Silverman J. Med. Chem. 45 2002 4531 4539
14. J. Qiu, and R.B. Silverman J. Med. Chem. 43 2000 706 720
15. W.M. Pardridge J. Neurovirol. 5 1999 556 569
16. P. Storici, G. Capitani, D. De Biase, M. Moser, R.A. John, J.N. Jansonius, and T. Schirmer Biochemistry 38 1999 8628 8634
17. S. Jeremiah, and S. Povey Ann. Hum. Genet. 45 1981 231 236
18. J.L. Kraus, P. Faury, A.S. Charvet, and M. Camplo Res. Commun. Mol. Pathol. Pharmacol. 83 1994 209 222
19. M.P. DeNinno, C. Eller, and J.B. Etienne J. Org. Chem. 66 2001 6988 6993
20. G. Brieger, and T. Nestrick J. Chem. Rev. 74 1974 567 580
21. J.T. Drummond, and G. Johnson Tetrahedron Lett. 29 1988 1653 1656
22. E.A. Wintner, B. Taso, and J. Rebek Jr. J. Org. Chem. 60 1995 7997 8001
23. K. Koguro, T. Oga, S. Mitsui, and R. Orita Synthesis 10 1998 910 914
24. Woolf, B., cited by Haldane, J.B.S.; Stern, K.G. Algemeine Chemie der Enzyme; Steinkopf: Dresden, 1932; pp 119-120
25. C.S. Hanes Biochem. J. 26 1932 1406 1421
26. R. Kitz, and I.B. Wilson J. Biol. Chem. 237 1962 3245 3249
27. T. Balle, J. Perregaard, A.K. Larsen, M.T. Ramirez, K.K. Soby, T. Liljefors, and K. Andersen Bioorg. Med. Chem. 11 2003 1065 1078
28. J.E. Churchich, and U. Moses J. Biol. Chem. 256 1981 1101 1104
29. D. Jeffery, P.D.J. Weitzman, and G.G. Lunt Insect Biochem. 28 1988 347 349
30. E.M. Scott, and W.B. Jakoby J. Biol. Chem. 234 1958 932 936