Use of the hydantoin isostere to produce inhibitors showing selectivity toward the vesicular glutamate transporter versus the obligate exchange transporter system

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 14, 2011, Pages 4358-4362

  Ahmed, S Kaleem ^a   Etoga, Jean Louis G ^a   Patel, Sarjubhai A ^a   Bridges, Richard J ^a   Thompson, Charles M ^a,b  

^a UNIVERSITY OF MONTANA   (United States)

^b ATERIS Technologies LLC   (United States)

Author keywords

Glutamate; Hydantoin scaffolds; Inhibitor; System; VGLUT

Indexed keywords

BENZENE 2,4 DISULFONIC ACID DERIVATIVE; BIS HYDANTOIN; CYSTINE GLUTAMATE TRANSPORTER; GLUTAMATE TRANSPORTER; HYDANTOIN DERIVATIVE; PARA DIAMINOBENZENE DERIVATIVE; PROTEIN INHIBITOR; THIOPHENE 5 CARBOXALDEHYDE DERIVATIVE; UNCLASSIFIED DRUG; VESICULAR GLUTAMATE TRANSPORTER;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG SELECTIVITY; DRUG SYNTHESIS;

AMINO ACID TRANSPORT SYSTEM Y+; GLUTAMIC ACID; HYDANTOINS; STRUCTURE-ACTIVITY RELATIONSHIP; VESICULAR GLUTAMATE TRANSPORT PROTEINS;

EID: 79959901157     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.05.018     Document Type: Article

References (32)

1. B. Meldrum Epilepsia 25 1984 S140 suppl. 2
2. B.S. Meldrum Neurology 44 1994 S14
3. B.S. Meldrum J. Nutr. 130 2000 1007S
4. S. Nakanishi Science 258 1992 597
5. D.D. Schoepp, and P. Conn J. Trends Pharmacol. Sci. 14 1993 13
6. P.H. Seeburg Trends Neurosci. 16 1993 359
7. J.C. Watkins, P.C. Pook, D.C. Sunter, J. Davies, and T. Honore Adv. Exp. Med. Biol. 268 1990 49
8. D.W. Choi, and S.M. Rothman Annu. Rev. Neurosci. 13 1990 171
9. G.T. Swanson, and R. Sakai Prog. Mol. Subcell. Biol. 46 2009 123
10. Y. Moriyama, and H. Omote Biol. Pharm. Bull. 31 2008 1844
11. S. Takamori Neurosci. Res. 55 2006 343
12. J. Burdo, R. Dargusch, and D. Schubert J. Histochem. Cytochem. 54 2006 549
13. M. Domercq, M.V. Sanchez-Gomez, C. Sherwin, E. Etxebarria, R. Fern, and C. Matute J. Immunol. 178 2007 6549
14. R.J. Bridges, M.P. Kavanaugh, and A.R. Chamberlin Curr. Pharm. Des. 5 1999 363
15. R.J. Bridges, F.E. Lovering, H. Koch, C.W. Cotman, and A.R. Chamberlin Neurosci. Lett. 174 1994 193
16. J.L. Etoga, S.K. Ahmed, S. Patel, R.J. Bridges, and C.M. Thompson Bioorg. Med. Chem. Lett. 20 2010 2680
17. S.A. Patel, T. Rajale, E. O'Brien, D.J. Burkhart, J.K. Nelson, B. Twamley, A. Blumenfeld, M.I. Szabon-Watola, J.M. Gerdes, R.J. Bridges, and N.R. Natale Bioorg. Med. Chem. 18 2010 202
18. C.N. Carrigan, R.D. Bartlett, C.S. Esslinger, K.A. Cybulski, P. Tongcharoensirikul, R.J. Bridges, and C.M. Thompson J. Med. Chem. 45 2002 2260
19. C.N. Carrigan, C.S. Esslinger, R.D. Bartlett, R.J. Bridges, and C.M. Thompson Bioorg. Med. Chem. Lett. 9 1999 2607
20. C.M. Thompson, E. Davis, C.N. Carrigan, H.D. Cox, R.J. Bridges, and J.M. Gerdes Curr. Med. Chem. 12 2005 2041
21. P. Barraclough, M.L. Bolofo, H. Giles, J. Gillam, C.J. Harris, M.G. Kelly, P. Leff, A. McNeill, A.D. Robertson, R.J. Stepney, and B.J. Whittle Bioorg. Med. Chem. 4 1996 81
22. W.C. Groutas, M.A. Stanga, J.C. Castrisos, and E.J. Schatz J. Enzyme Inhib. 3 1990 237
23. N.A. Meanwell, H.R. Roth, E.C. Smith, D.L. Wedding, J.J. Wright, J.S. Fleming, and E. Gillespie J. Med. Chem. 34 1991 2906
24. R. Sarges, and P.J. Oates Prog. Drug Res. 40 1993 99
25. J.J. Li Name Reactions 2009 Springer Berlin Heidelberg p 76
26. Synthesis of compounds 4a-b. To approx. 2.0 g of carbonyl compound (0.02 mol) dissolved in 50% methanol (50 mL) were added ammonium carbonate (9.1 g; 0.08 mol) and potassium cyanide (2.6 g; 0.04 mol). The mixture was warmed to 58-60 °C for 3 h, concentrated to 15 mL, and chilled to 0 °C to produce white-off yellow crystals.
27. S.A. Patel, B.A. Warren, J.F. Rhoderick, and R.J. Bridges Neuropharmacology 46 2004 273
28. P.E. Kish, and T. Ueda Methods Enzymol. 174 1989 9
29. C.S. Esslinger, S. Agarwal, J. Gerdes, P.A. Wilson, E.S. Davis, A.N. Awes, E. O'Brien, T. Mavencamp, H.P. Koch, D.J. Poulsen, J.F. Rhoderick, A.R. Chamberlin, M.P. Kavanaugh, and R.J. Bridges Neuropharmacology 49 2005 850
30. Chappell, M. D. P. D.; Conner, S. E.; Tripp, A. E.; Zhu, G. WO/2006/086488, Substituted Thiophene Derivatives as Glucagon Receptor Antagonists, Preparation and Therapeutic Uses, 2006.
31. I.C. Choong, W. Lew, D. Lee, P. Pham, M.T. Burdett, J.W. Lam, C. Wiesmann, T.N. Luong, B. Fahr, W.L. DeLano, R.S. McDowell, D.A. Allen, D.A. Erlanson, E.M. Gordon, and T. O'Brien J. Med. Chem. 45 2002 5005
32. M. Shilai, Y. Kondo, and T. Sakamoto J. Chem. Soc., Perkin Trans. 1 2001 442