Synthesis of [O-methyl-11C]1-(2-chlorophenyl)-5-(4- methoxyphenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide: A potential PET ligand for CB1 receptors

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 10, 2004, Pages 2393-2396

  Kumar, J S Dileep ^a,b   Prabhakaran, Jaya ^a   Arango, Victoria ^a,b   Parsey, Ramin V ^a,b   Underwood, Mark D ^a,b   Simpson, Norman R ^a,b   Kassir, Suham A ^b   Majo, Vattoly J ^a   Van Heertum, Ronald L ^a,b   Mann, J John ^a,b  

^a Columbia Univ Coll Phys Surgs ^*  (United States)

^b NEW YORK STATE PSYCHIATRIC INSTITUTE   (United States)

Author keywords

Autoradiography; Biological imaging; CB1 receptors; Human postmortem; Positron emission tomography

Indexed keywords

1 (2 CHLOROPHENYL) 5 (4 METHOXYPHENYL) 4 METHYL 1H PYRAZOLE 3 CARBOXYLIC ACID PIPERIDIN 1 YLAMIDE C 11; CANNABINOID 1 RECEPTOR; TRACER; UNCLASSIFIED DRUG;

ACCURACY; ARTICLE; AUTORADIOGRAPHY; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; ENERGY YIELD; HUMAN; HUMAN TISSUE; IMAGING SYSTEM; IN VITRO STUDY; POSITRON EMISSION TOMOGRAPHY; PREFRONTAL CORTEX; RADIOCHEMISTRY; REACTION ANALYSIS; STRUCTURE ANALYSIS; TEMPERATURE DEPENDENCE;

AUTORADIOGRAPHY; BRAIN CHEMISTRY; CARBON RADIOISOTOPES; HUMANS; LIGANDS; PIPERIDINES; POSITRON-EMISSION TOMOGRAPHY; PYRAZOLES; RADIOPHARMACEUTICALS; RECEPTOR, CANNABINOID, CB1;

EOS;

EID: 11144353911     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.03.034     Document Type: Article

References (24)

1. Rudgley, R.; Brown, L. http://www.cannabis.net/hist/ (website accessed September 20, 2003).
2. Baker D., Pryle G., Glovannoni G., Thomson A.J. Lancet. 2:2003;291.
3. Howlett A.C., Bonner B.F., Casellas C.G., Devane W.A., Felder C.C., Herkenham M., Martin M.K., Mechoulam R., Pertwee R.G. Pharmacol. Rev. 54:2003;161.
4. Glass M., Dragunow M., Faull R.L. Neuroscience. 77:1997;299.
5. Croxford J.L. CNS Drugs. 17:2003;179.
6. Whittle B.A., Guy G.W., Robson P. J. Cannabis Ther. 1:2001;183.
7. Williamson E.M., Evans F.J. Drugs. 60:2000;1303.
8. Pertwee R.G. Pharm. Sci. 3:1997;539.
9. Grundy R.I. Expert Opin. Invest. Drugs. 11:2002;1365.
10. Seitz R. Dtsch. Apoth. Ztg. 142:2002;140.
11. Hungund B.L., Vinod K.Y., Kassir S.A., Basavarajappa B.A., Yalamanchilli R., Cooper T.B., Mann J.J., Arango V.A. Mol. Psychiatry. 9:2004;184-190.
12. Vinod, K. Y.; Arango, U.; Xie, X.; Kassir, S. A.; Mann, J. J.; Cooper, T. B.; Hungung, B. L. Am. J. Psychiatry 2004, submitted for publication.
13. Marciniak G., Charalambous A., Shiue C.Y., Dowey S.L., Schlyer D.J., Makriyannis A., Wolf A.P. J. Label. Compd. 30:1991;413.
14. Charalambous A., Marciniak G., Shiue C.Y., Dowey S.L., Schlyer D.J., Wolf A.P., Makriyannis A. Pharmacol. Biochem. Behav. 40:1991;503.
15. Gifford A.N., Makriyannis A., Volkow N.D., Gatley S.J. Chem. Phys. Lipids. 121:2002;65.
16. Mathews W.B., Scheffel U., Finley P., Ravert H.T., Frank R.A., Carmona M.R., Barth F., Dannals R.F. Nucl. Med. Biol. 27:2000;757.
17. Mathews W.B., Scheffel U., Rauseo P.A., Ravert H.T., Frank R.A., Ellames G.J., Herbert J.M., Barth F., Rinaldi C.M., Dannals R.F. Nucl. Med. Biol. 29:2002;671.
18. D'Ambra T.E., Estep K.G., Bell M.R., Eissenstat M.A., Josef K.A., Ward S.J., Haycock D.A., Baizman E.R., Casiano F.M., Beglin N.C. J. Med. Chem. 35:1992;124.
19. Willis P.G., Katoch R.R., Horti A.G. J. Label. Compd. Radiopharm. 46:2003;799.
20. LaVerne B.L., Kulkarni S., Pavlova O.A., Koren A.O., Mukhin A.G., Newman A.H., Horti A.G. J. Med. Chem. 46:2003;642.
21. 4Cl 411.1588; found 411.1601.
22. 11C]-1 was analyzed with analytical HPLC for chemical identity, chemical and radiochemical purities, and specific activity. The average yield was found to be 14.5% at EOS with a specific activity >2000 Ci/mmol.
23. 14C] standards (American Radiolabeled Chemicals) for 90 min. Screens were scanned with a Packard Cyclone phosphor-imaging system and analyzed with OptiQuant Acquisition and Analysis software (Packard).
24. Rinaldi C.M., Barth F., Heaulme M., Shire D., Calandra B., Congy C., Martinez S., Maruani J., Neliat G., Caput D. FEBS Lett. 350:1994;240.