Synthesis of σ receptor ligands with unsymmetrical spiro connection of the piperidine moiety

European Journal of Medicinal Chemistry

Volumn 44, Issue 11, 2009, Pages 4306-4314

  Jasper, Annemarie ^a   Schepmann, Dirk ^a   Lehmkuhl, Kirstin ^a   Vela, Jose Miguel ^b   Buschmann, Helmut ^b   Holenz, Jörg ^b   Wünsch, Bernhard ^a  

^a Institut für Pharmazeutische und Medizinische Chemie   (Germany)

^b ESTEVE   (Spain)

Author keywords

Receptor ligands; Halogen metal exchange; Receptor binding studies; Spirocyclic piperidines; Structure affinity relationships; Transmetallation

Indexed keywords

1' BENZYL 3 METHOXY 3,4 DIHYDROSPIRO[[2]BENZOPYRAN 1,3' PIPERIDINE]; 1' BUTYL 3 METHOXY 3,4 DIHYDROSPIRO[[2]BENZOPYRAN 1,3' PIPERIDINE]; 1' DECYL 3 METHOXY 3,4 DIHYDROSPIRO[[2]BENZOPYRAN 1,3' PIPERIDINE]; 1' HEXYL 3 METHOXY 3,4 DIHYDROSPIRO[[2]BENZOPYRAN 1,3' PIPERIDINE]; 3 METHOXY 1' (2 PHENYLETHYL) 3,4 DIHYDROSPIRO[[2]BENZOPYRAN 1,3' PIPERIDINE]; 3 METHOXY 1' (3 PHENYLPROPYL) 3,4 DIHYDROSPIRO[[2]BENZOPYRAN 1,3' PIPERIDINE]; 3 METHOXY 1' (4 PHENYLBUTYL) 3,4 DIHYDROSPIRO[[2]BENZOPYRAN 1,3' PIPERIDINE]; 3 METHOXY 1' OCTYL 3,4 DIHYDROSPIRO[[2]BENZOPYRAN 1,3' PIPERIDINE]; 3 METHOXY 3,4 DIHYDROSPIRO[[2]BENZOPYRAN 1,3' PIPERIDINE]; HALOGEN; METAL; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; NITROGEN; PIPERIDINE; PIPERIDONE DERIVATIVE; SIGMA 1 OPIATE RECEPTOR; SIGMA 2 OPIATE RECEPTOR; SIGMA RECEPTOR LIGAND; SPIRO[[2]BENZOPYRAN 1,3' PIPERIDINE DERIVATIVE]; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; NONHUMAN; NUCLEAR OVERHAUSER EFFECT; RECEPTOR AFFINITY; RECEPTOR BINDING; STEREOCHEMISTRY; SYNTHESIS;

ANIMALS; GUINEA PIGS; MOLECULAR STRUCTURE; PIPERIDINES; PROTEIN BINDING; RATS; RECEPTORS, SIGMA; SPIRO COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 70349766699     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.07.017     Document Type: Article

References (31)

1. Martin W.R., Eades C.G., Thornpson W.O., Huppler R.E., and Glibert P.E. J. Pharmacol. Exp. Ther. 197 (1976) 517-532
2. Kaiser C., Pontecorvo M., and Mewshaw R.E. Neurotransinissions 7 (1991) 1-5
3. Zukin S.R., Tempel A.L., and Zukein R.S. J. Neurosci. 46 (1986) 1032-1041
4. Gundlach A.L., Largent B.L., and Snyder S.H. Eur. J. Pharmacol. 113 (1985) 465-466
5. Su T.P. Sigma Receptors in the Central Nervous System and the Periphery. In: Itzhak Y. (Ed). The Sigma Receptors (1994), Academic Press, London pp. 21-44
6. Hellewell S.B., Bruce A., Feinstein G., Orringer J., Williams W., and Bowen W.D. Eur. J. Pharmacol. 268 (1994) 9-18
7. Kekuda R., Prasad P.D., Fei Y.J., Leibach F.H., and Ganapathy V. Biochem. Biophys. Res. Commun. 229 (1996) 553-558
8. Aydar E., Palmer C.P., Klachko V.A., and Jackson M.B. Neuron 31 (2002) 399-410
9. Seth P., Leibach F.H., and Ganapathy V. Biophys. Res. Commun. 241 (1997) 535-540
10. Moebius F.F., Striessnig I., and Glossmann H. Trends Pharmacol. Sci. 18 (1997) 67-70
11. Taylor D.P., Shukla U.A., Wolfe S.A., Owen P.Q., Pyke R., et al. Schizophrenia Res. 4 (1991) 327
12. Urani A., Romieu P., Roman F., Yamada K., Noda Y., et al. Eur. J. Pharmacol. 486 (2004) 15-16
13. Marrazzo A., Caraci F., Salinaro E.T., Su T.P., Copani A., et al. Neuroreport 16 (2005) 1223-1226
14. John C.S., Lim B.B., Geyer B.C., Vilner B.J., and Bowen W.D. Bioconjug. Chem. 8 (1997) 304-309
15. Vilner B.J., John C.S., and Bowen W.D. Cancer Res. 55 (1995) 408-413
16. Caveliers V., Everaert H., John C.S., Lahoutte T., and Bossuyt A. J. Nucl. Med. 43 (2002) 1647-1649
17. Maier C.A., and Wünsch B. J. Med. Chem. 45 (2002) 438-448
18. Wünsch B. Arch. Pharm. 323 (1990) 493-499
19. Wünsch B., Höfner G., and Bauschke G. Arch. Pharm. 326 (1993) 513-518
20. Macchia B., Macchia M., Manera C., Martinotti E., Nencetti S., et al. Eur. J. Med. Chem. 30 (1995) 869-880
21. Varchi G., Kofink C., Lindsav D.M., Ricci A., and Knochel P. Chem. Commun. 3 (2003) 396-397
22. Kaiser F., Schwink L., Velder J., and Schmalz H.G. J. Org. Chem. 67 (2002) 9248-9256
23. Ram S., and Spicer L.D. Tetrahedron Lett. 28 (1987) 515-516
24. Hayes B.L. Microwave Synthesis (2002), CEM Publishing
25. DeHaven-Hudkins D.L., Fleissner L.C., and Ford-Rice F.Y. Eur. J. Pharmacol. Mol. 227 (1992) 371-378
26. Wirt U., Schepmann D., and Wünsch B. Eur. J. Org. Chem. (2007) 462-475
27. Mach R.H., Smits C.R., and Childers S.R. Life Sci. 57 (1995) 57-62
28. Glennon R.A., Ablordeppey S.Y., Ismaiel A.M., El-Ashmawy M.B., Fischer J.B., and Howie K.B. J. Med. Chem. 37 (1994) 1214-1219
29. Glennon R.A. Minirev. Med. Chem. 5 (2005) 927-940
30. Bradford M.M. Anal. Biochem. 72 (1976) 248-254
31. Cheng Y.C., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099-3108