Synthesis and structure-activity relationships (SARs) of 1,5-diarylpyrazole cannabinoid type-1 (CB1) receptor ligands for potential use in molecular imaging

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 11, 2006, Pages 3712-3720

  Donohue, Sean R ^a,b   Halldin, Christer ^b   Pike, Victor W ^a  

^a NATIONAL INSTITUTE OF MENTAL HEALTH   (United States)

^b KAROLINSKA INSTITUTE   (Sweden)

Author keywords

1,5 Diarylpyrazoles; Carbon 11; CB1 receptor; NIDA 41087; PET; Rimonabant

Indexed keywords

CANNABINOID 1 RECEPTOR; N (PIPERIDIN 1 YL) 1 (2 BROMOPHENYL) 5 (4 METHOXYPHENYL) 4 METHYL 1H PYRAZOLE 3 CARBOXAMIDE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BLOOD BRAIN BARRIER; DRUG POTENCY; DRUG SYNTHESIS; LIGAND BINDING; LIPOPHILICITY; MOLECULAR DYNAMICS; MOLECULAR IMAGING; MOLECULAR PROBE; NEUROIMAGING; POSITRON EMISSION TOMOGRAPHY; RECEPTOR BINDING; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; STRUCTURE ACTIVITY RELATION;

DRUG DESIGN; HUMANS; IMAGING, THREE-DIMENSIONAL; LIGANDS; MOLECULAR STRUCTURE; PYRAZOLES; RECEPTOR, CANNABINOID, CB1; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33646043443     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.01.047     Document Type: Article

References (32)

1. Howlett A.C., Barth F., Bonner T.I., Cabral G., Casellas P., Devane W.A., Felder C.C., Herkenham M., Mackie K., Martin B.R., Mechoulam R., and Pertwee R.G. Pharmacol. Rev. 54 (2002) 161-202
2. Howlett A.C., Qualy J.M., and Khachatrian L.L. Mol. Pharmacol. 29 (1986) 307-313
3. Herkenham M., Lynn A.B., Little M.D., Johnson M.R., Melvin L.S., de Costa B.R., and Rice K.C. Proc. Natl. Acad. Sci. U.S.A. 87 (1990) 1932-1936
4. Glass M., Dragunow M., and Faull R.L. Neuroscience 77 (1997) 299-318
5. Croci T., Manara L., Aureggi G., Guagnini F., Rinaldi-Carmona M., Maffrand J.P., Le Fur G., Mukenge S., and Ferla G. Br. J. Pharmacol. 125 (1998) 1393-1395
6. Straiker A.J., Maguire G., Mackie K., and Lindsey J. Invest. Ophthalmol. Vis. Sci. 40 (1999) 2442-2448
7. Gye M.C., Kang H.H., and Kang H.J. Arch. Androl. 51 (2005) 247-255
8. Pertwee R.G., and Fernando S.R. Br. J. Pharmacol. 118 (1996) 2053-2058
9. Klein T.W., Newton C., and Friedman H. Immunol. Today 19 (1998) 373-381
10. Galiègue S., Mary S., Marchand J., Dussossoy D., Carrière D., Carayon P., Bouaboula M., Shire D., Le Fur G., and Casellas P. Eur. J. Biochem. 232 (1995) 54-61
11. Haller J., Varga B., Ledent C., and Freund T.F. Behav. Pharmacol. 15 (2004) 299-304
12. Le Foll B., and Goldberg S.R. J. Pharmacol. Exp. Ther. 312 (2005) 875-883
13. Vinod K.Y., Arango V., Xie S., Kassir S.A., Mann J.J., Cooper T.B., and Hungund B.L. Biol. Psychiatry 57 (2005) 480-486
14. Lastres-Becker I., Berrendero F., Lucas J.J., Martin-Aparicio E., Yamamoto A., Ramos J.A., and Fernández-Ruiz J.J. Brain Res. 929 (2002) 236-242
15. Muller-Vahl K.R. Expert Opin. Pharmacother. 4 (2003) 1717-1725
16. Rinaldi-Carmona M., Barth F., Heaulme M., Shire D., Calandra B., Congy C., Martinez S., Maruani J., Neliat G., Caput D., Ferrara T., Soubrié P., Breliere J.C., and Le Fur G. FEBS Lett. 350 (1994) 240-244
17. Lan R.X., Liu Q., Fan P.S., Lin S.Y., Fernando S.R., McCallion D., Pertwee R., and Makriyannis A. J. Med. Chem. 42 (1999) 769-776
18. Wiley J.L., Jefferson R.G., Grier M.C., Mahadevan A., Razdan R.K., and Martin B.R. J. Pharmacol. Exp. Ther. 296 (2001) 1013-1022
19. Thomas B.F., Francisco M.E., Seltzman H.H., Thomas J.B., Fix S.E., Schulz A.K., Gilliam A.F., Pertwee R.G., and Stevenson L.A. Bioorg. Med. Chem. 13 (2005) 5463-5474
20. Shim J.Y., Welsh W.J., Cartier E., Edwards J.L., and Howlett A.C. J. Med. Chem. 45 (2002) 1447-1459
21. Katoch-Rouse R., Pavlova O.A., Caulder T., Hoffman A.F., Mukhin A.G., and Horti A.G. J. Med. Chem. 46 (2003) 642-645
22. Reggio P.H. Curr. Pharm. Des. 9 (2003) 1607-1633
23. Gatley S.J., Gifford A.N., Volkow N.D., Lan R., and Makriyannis A. Eur. J. Pharmacol. 307 (1996) 331-338
24. Gatley S.J., Lan R., Volkow N.D., Pappas N., King P., Wong C.T., Gifford A.N., Pyatt B., Dewey S.L., and Makriyannis A. J. Neurochem. 70 (1998) 417-423
25. Berding G., Müller-Vahl K., Schneider U., Gielow P., Fitschen J., Stuhrmann M., Harke H., Buchert R., Donnerstag F., Hofmann M., Knoop B.O., Brooks D.J., Emrich H.M., and Knapp W.H. Biol. Psychiatry 55 (2004) 904-915
26. Mathews W.B., Scheffel U., Finley P., Ravert H.T., Frank R.A., Rinaldi-Carmona M., Barth F., and Dannals R.F. Nucl. Med. Biol. 27 (2000) 757-762
27. Mathews W.B., Scheffel U., Rauseo P.A., Ravert H.T., Frank R.A., Ellames G.J., Herbert J.M., Barth F., Rinaldi-Carmona M., and Dannals R.F. Nucl. Med. Biol. 29 (2002) 671-677
28. Pike V.W. J. Psychopharmacol. 7 (1993) 139-158
29. Waterhouse R.N. Mol. Imaging Biol. 5 (2003) 376-389
30. Li Z., Gifford A., Liu Q., Thotapally R., Ding Y.S., Makriyannis A., and Gatley S.J. Nucl. Med. Biol. 32 (2005) 361-366
31. Kumar J.S., Prabhakaran J., Arango V., Parsey R.V., Underwood M.D., Simpson N.R., Kassir S.A., Majo V.J., Van Heertum R.L., and Mann J.J. Bioorg. Med. Chem. Lett. 14 (2004) 2393-2396
32. DeLapp N.W., McKinzie J.H., Sawyer B.D., Vandergriff A., Falcone J., McClure D., and Felder C.C. J. Pharmacol. Exp. Ther. 289 (1999) 946-955