Synthesis of spirocyclic σ1 receptor ligands as potential PET radiotracers, structure-affinity relationships and in vitro metabolic stability

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 10, 2009, Pages 3630-3641

  Große Maestrup, Eva ^a   Wiese, Christian ^a   Schepmann, Dirk ^a   Hiller, Achim ^b   Fischer, Steffen ^b   Scheunemann, Matthias ^b   Brust, Peter ^b   Wünsch, Bernhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b Institut fur Interdisziplinare Isotopenforschung   (Germany)

Author keywords

1 Receptor antagonists; 18F Radiotracer; Metabolism; Neuroimaging; Spirocyclic piperidines; Structure affinity relationships

Indexed keywords

1' (4 FLUOROBENZYL) 3 METHOXY 3H SPIRO([2]BENZOFURAN 1,4' PIPERIDINE); 1' (4 FLUOROBENZYL) 3 METHOXY 3H SPIRO([2]BENZOFURAN 1,4' PIPERIDINE) F 18; 1' (4 FLUOROBENZYL) 3H SPIRO([2]BENZOFURAN 1,4' PIPERIDINE); 1' (4 FLUOROBENZYL) 3H SPIRO([2]BENZOFURAN 1,4' PIPERIDINE) 3 CARBONITRILE; 1' (4 FLUOROBENZYL) 3H SPIRO([2]BENZOFURAN 1,4' PIPERIDINE) 3 CARBONITRILE F 18; 3H SPIRO([2]BENZOFURAN 1,4' PIPERIDINE) DERIVATIVE; BENZALDEHYDE DERIVATIVE; BENZOFURAN DERIVATIVE; FLUORINE 18; LITHIUM; NITROGEN; OPIATE RECEPTOR AFFECTING AGENT; SIGMA 1 OPIATE RECEPTOR; SPIRO[BENZOFURANPIPERIDINE]; TRACER; UNCLASSIFIED DRUG; CYTOCHROME P450; PIPERIDINE DERIVATIVE; RADIOPHARMACEUTICAL AGENT; SIGMA 2 OPIATE RECEPTOR; SIGMA OPIATE RECEPTOR; SIGMA-1 RECEPTOR; SIGMA-2 RECEPTOR; SPIRO COMPOUND;

ANIMAL TISSUE; ARTICLE; BRAIN; CATALYSIS; DRUG DEGRADATION; DRUG RECEPTOR BINDING; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; GUINEA PIG; HUMAN; LIVER MICROSOME; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; RAT; REACTION ANALYSIS; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; ANIMAL; CHEMISTRY; DRUG ANTAGONISM; METABOLISM; SYNTHESIS;

RATTUS;

ANIMALS; CYTOCHROME P-450 ENZYME SYSTEM; DRUG STABILITY; GUINEA PIGS; HUMANS; PIPERIDINES; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RATS; RECEPTORS, SIGMA; SPIRO COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 65349159284     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.03.060     Document Type: Article

References (36)

1. Danso-Danquah R., Bai X., Zhang X., Mascarella S.W., Williams W., Sine B., Bowen W.D., and Carroll F.I. J. Med. Chem. 38 (1995) 2978
2. Kaiser C., Pontecorvo J., and Mewshaw R.E. Neurotransmission 7 (1991) 1
3. Walker J.M., Bowen W.D., Walker F.O., Matsumoto R.R., De Costa B., and Rice K.C. Pharmacol. Rev. 42 (1990) 353
4. Rowley M., Bristow L.J., and Hutson P.H. J. Med. Chem. 44 (2001) 477
5. Monograph Igmesine Hydrochloride, Drugs Future 1999, 24, 133.
6. Skuza G. Pol. J. Pharmacol. 55 (2003) 923
7. Maurice T., and Lockhart B.P. Prog. Neuropsychopharmacol. Biol. Psychiat. 21 (1997) 69
8. Marrazzo A., Caraci F., Salinaro E.T., Su T.P., Copani A., and Ronsisvalle G. Neuroreport 18 (2005) 1223
9. Gilchrist H.D., Allard B.L., and Simone D.A. Pain 67 (1996) 179
10. Baeyens, J. M. PCT Int. Appl. 2006, WO 2006/010587 A1.
11. Matsumoto R.R., Liu Y., Lerner M., Howard E.W., and Brackett D.J. Eur. J. Pharmacol. 496 (2003) 1
12. Hayashi T., and Su T.-P. CNS Drugs 18 (2004) 269
13. Meunier J., Ieni J., and Maurice T. Br. J. Pharmacol. 149 (2006) 998
14. Bermack J.E., and Debonnel G. Synapse 55 (2005) 37
15. Gudelsky G.A. J. Neural. Trans. 106 (1999) 849
16. Bowen W.D. Pharm. Acta Helv. 74 (2000) 211
17. Wilke R.A., Lupardus P.J., Grandy D.K., Rubinstein M., Low M.J., and Jackson M.B. J. Physiol. 517 (1999) 391
18. Aydar E., Palmer C.P., and Djamgoz M.B.A. Cancer Res. 64 (2004) 5029
19. Monnet F.P. Biol. Cell 97 (2005) 873
20. Zhang H., and Cuevas J. J. Neurophysiol. 87 (2002) 2867
21. Maier C.A., and Wünsch B. J. Med. Chem. 45 (2002) 438
22. Maier C.A., and Wünsch B. J. Med. Chem. 45 (2002) 4923
23. Wiese C., Große Maestrup E., Schepmann D., Vela J.M., Holenz J., Buschmann H., and Wünsch B. J. Pharm. Pharmacol. 61 (2009) 631
24. Ley S.V., Norman J., Griffith W.P., and Marsden S.P. Synthesis (1994) 639
25. Brückner, Reaktionsmechanismen, 3rd ed., Elsevier GmbH, 2004, p 797.
26. Cohen N., Schaer B., Saucy G., Borer R., Todaro L., and Chiu A.-M. J. Org. Chem. 54 (1989) 3282
27. Komatsu N., Uda M., Suzuki H., Takahashi T., Domae T., and Wada M. Tetrahedron Lett. (1997) 7215
28. Wirt U., Schepmann D., and Wünsch B. Eur. J. Org. Chem. (2007) 462
29. Haka M.S., Kilbourn R., Watkins G.L., and Toorongian S.A. J. Label. Comp. Radiopharm. 27 (1989) 823
30. Wilson A.A., Dannanls R.F., Hayden T.R., and Wagner H.N. J. Label. Comp. Radiopharm. 28 (1990) 1189
31. Bradford M.M. Anal. Biochem. 72 (1976) 248
32. De-Haven-Hudkins D.L., Fleissner L.C., and Ford-Rice F.Y. Eur. J. Pharmacol. Mol. Pharmacol. Sect. 227 (1992) 371
33. Mach R.H., Smith C.R., and Childers S.R. Life Sci. 57 (1995) 57
34. Cheng Y.-C., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099
35. Dayer P., and Gasser R. Biochem. Biophys. Res. Commun. 30 (1984) 374
36. Unpublished results, manuscript in preparation.