Synthesis and pharmacological evaluation of Tic-hydantoin derivatives as selective σ1 ligands. Part 1

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 21, 2005, Pages 4833-4837

  Charton, Julie ^a   Gassiot, Amaury Cazenave ^a,b   Girault Mizzi, Sophie ^a   Debreu Fontaine, Marie Ange ^a   Melnyk, Patricia ^a   Sergheraert, Christian ^a  

^a CNRS   (France)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

Author keywords

receptors; Hydantoin; Selectivity; Tic

Indexed keywords

HALOPERIDOL; HYDANTOIN DERIVATIVE; SIGMA 1 OPIATE RECEPTOR; SIGMA RECEPTOR LIGAND; TETRAHYDROISOQUINOLINE DERIVATIVE;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; GUINEA PIG; IC 50; NONHUMAN; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIDEPRESSIVE AGENTS; CELL SURVIVAL; GUINEA PIGS; HYDANTOINS; INHIBITORY CONCENTRATION 50; LIGANDS; RECEPTORS, SIGMA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 25144517818     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.07.040     Document Type: Article

References (39)

1. J. Karolak-wojciechowska, W. Kwiatkowski, and K. Kieckonono Pharmazie 50 1995 114
2. W.J. Brouillette, G.B. Brown, T.M. DeLorey, and G. Liang J. Pharm. Sci 79 1990 871
3. W.J. Brouillette, V.P. Jestkov, M.L. Brown, M.S. Akhtar, T.M. DeLorey, and G.B. Brown J. Med. Chem. 37 1994 3289
4. S. Vendeville, E. Buisine, X. Williard, J. Schrevel, P. Grellier, J. Santana, and C. Sergheraert Chem. Pharm. Bull. 47 1999 194
5. B. Déprez, X. Williard, L. Bourel, H. Coste, F. Hyafil, and A. Tartar J. Am. Chem. Soc. 117 1995 5405
6. J. Charton, S. Delarue, S. Vendeville, M.-A. Debreu-Fontaine, S. Girault-Mizzi, and C. Sergheraert Tetrahedron Lett. 42 2001 7559
7. 2 receptor for which compound 3a produced 63% inhibition at 10 μM and 5% inhibition at 0.1 μM.
8. W.D. Bowen Pharm. Acta Helv. 74 2000 211
9. M. Hanner, F.F. Moebius, A. Flandorfer, H.G. Knaus, J. Striessnig, E. Kempner, and H. Glossmann Proc. Natl. Acad. Sci. U.S.A. 93 1996 8072
10. R. Kekuda, P.D. Prasad, Y.J. Fei, F.H. Leibach, and V. Ganapathy Biochem. Biophys. Res. Commun. 229 1996 553
11. P.D. Prasad, H.W. Li, Y.J. Fei, M.E. Ganapathy, T. Fujita, L.H. Plumley, T.L. Yang-Feng, F.H. Leibach, and V. Ganapathy J. Neurochem. 70 1998 443
12. J. Mei, and G.W. Pasternak Biochem. Pharmacol. 62 2001 349
13. K. Senda, K. Matsuno, K. Okamoto, T. Kobajashi, K. Nakata, and S. Mita Eur. J. Pharmacol. 315 1996 1
14. K. Senda, K. Matsuno, T. Kobajashi, M. Nakazawa, K. Nakata, and S. Mita Pharmacol. Biochem. Behav. 59 1998 129
15. H. Kamei, Y. Noda, T. Kameyama, and T. Nabeshima Eur. J. Pharmacol. 319 1997 165
16. R. Bergeron, C. de Montigny, and G. Debonnel J. Neurosci. 16 1996 1193
17. T. Maurice, and A. Privat Eur. J. Pharmacol. 328 1997 9
18. G. Skuza Pol. J. Pharmacol. 55 2003 923
19. T. Maurice, R. Martin-Fardon, P. Romieu, and R.R. Matsumoto Neurosci. Biobehav. Rev. 26 2002 499
20. X. Guitart, X. Codony, and X. Monroy Psychopharmacology 174 2004 301
21. S.B. Hellewell, A. Bruce, G. Feinstein, J. Orringer, W. Williams, and W.D. Bowen Eur. J. Pharmacol. 268 1994 9
22. A. Marrazzo, O. Prezzavento, M.S. Pappalardo, E. Bousquet, M. Iadanza, V.W. Pike, and G. Ronsisvalle Il Farmaco 57 2002 45
23. B.J. Vilner, B.R. de Costa, and W.D. Bowen J. Neurosci. 15 1995 117
24. D.Y. Maeda, W. Williams, W.D. Bowen, and A. Coop Bioorg. Med. Chem. Lett. 10 2000 17
25. Y. Huang, P.S. Hammond, L. Wu, and R.H. Mach J. Med. Chem. 44 2001 4404
26. S. Chaki, M. Tanaka, M. Muramatsu, and S. Otomo Eur. J. Pharmacol. 251 1994 R1
27. F. Berardi, S. Santoro, R. Perrone, V. Tortorella, S. Govoni, and L. Lucchi J. Med. Chem. 41 1998 3940
28. J. Charton, A. Cazenave Gassiot, P. Melnyk, S. Girault-Mizzi, and C. Sergheraert Tetrahedron Lett. 45 2004 7081
29. D. Damour, M. Barreau, J.-C. Blanchard, M.-C. Burgevin, and A. Doble Chem. Lett. 9 1998 943
30. S.D. Burke, and R.L. Danheiser Handbook of Reagents for Organic Synthesis. Oxidizing and Reducing Agents 1999 John Wiley & Sons Chichester pp 199-200
31. M.F. Brana, M. Garrido, M. Luz Lopez, P. de Miguel, and A. Riano Synth. Commun. 20 1990 1793
32. K. Verschueren, G. Toth, D. Tourwé, M. Lebl, G. Van Binst, and V. Hruby Synthesis 1992 458
33. 35.
34. W.D. Bowen, B.R. de Costa, S.B. Hellewell, M. Walker, and K.C. Rice Mol. Neuropharmacol. 3 1993 117
35. M.E. Ganapathy, P.D. Prasad, W. Huang, P. Seth, F.H. Leibach, and V. Ganapathy J. Pharmacol. Exp. Ther. 289 1999 251
36. 4 buffer (pH 7.5) for 120 min at 22°C. Nonspecific binding was determined under similar conditions but in the presence of 10 μM unlabelled haloperidol.
37. 50 values from competitive inhibition experiments were determined using the Marquardt-Levenberg nonlinear curve fitting procedure of Xfit macro (Microsoft Excel).
38. R.C.A. Onderwater, J.N.M. Commandeur, E.J. Groot, A. Sitters, W.M.P.B. Menge, and N.P.E. Vermeulen Toxicology 125 1998 117
39. R.A. Glennon, S.Y. Ablordeppey, A.M. Ismael, M.B. El-Ashmawy, J.B. Fisher, and K.B. Howie J. Med. Chem. 37 1994 1214