Synthesis and CB1 cannabinoid receptor affinity of 4-alkoxycarbonyl-1,5-diaryl-1,2,3-triazoles

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 3, 2009, Pages 891-893

  Shu, Hong ^a   Izenwasser, Sari ^b   Wade, Dean ^b   Stevens, Edwin D ^a   Trudell, Mark L ^a  

^a UNIVERSITY OF NEW ORLEANS   (United States)

^b UNIVERSITY OF MIAMI MILLER SCHOOL OF MEDICINE   (United States)

Author keywords

Cannabinoid receptors; Click chemistry; Triazoles

Indexed keywords

CANNABINOID 1 RECEPTOR; CANNABINOID 1 RECEPTOR AGONIST; RIMONABANT; TRIAZOLE DERIVATIVE;

ARTICLE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; RECEPTOR AFFINITY; STEREOCHEMISTRY;

CENTRAL NERVOUS SYSTEM; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; ESTERS; GENE EXPRESSION REGULATION; HUMANS; KINETICS; LIGANDS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PROTEIN BINDING; PYRAZOLES; RECEPTOR, CANNABINOID, CB1; TRIAZOLES;

EID: 58549099845     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.11.110     Document Type: Article

References (38)

1. Devane W.A., Dysarz F.A., Johnson M.R., Melvin L.S., and Howlett A.C. Mol. Pharmacol. 34 (1988) 605
2. Matsuda L.A., Lolait S.J., Brownstein M.J., Young A.C., and Bonner T.I. Nature 346 (1990) 561
3. Munro S., Thomas K.L., and Abu-Shaar M. Nature (1993) 61
4. Gerard C.M., Mollereau C., Vassart G., and Parmentier M. Biochem. J. 279 (1991) 129
5. Herkenham M., Lynn A.B., Little M.D., Johnson M.R., Melvin L.S., and de Costa B.R. Proc. Natl. Acad. Sci. U.S.A. 87 (1990) 1932
6. Herkenham M., Lynn A.B., de Costa B.R., and Richfield E.K. Brain Res. 547 (1991) 267
7. Herkenham M., Lynn A.B., Johnson M.R., Melvin L.S., de Costa B.R., and Rice K.C. J. Neurosci. 11 (1991) 563
8. Mailleux P., and Vanderhaeghen J.J. Neuroscience 48 (1992) 655
9. Howlett A.C., Qualy J.M., and Khachatrian L.L. Mol. Pharmacol. 29 (1986) 307
10. Herkenham M. In: Pertwee R.G. (Ed). Cannabinoid Receptors (1995), Academic Press, New York p 145
11. Howlett A.C., Barth F., Bonner T.I., Cabral G., Casellas P., and Devane W.A. Pharmacol. Rev. 54 (2002) 161
12. Onaivi E.S., Ishiguro H., Gong J.P., Patel S., Perchuk A., Meozzi P.A., Myers L., Mora Z., Tagliaferro P., Gardner E., Brusco A., Akinshola B.E., Liu Q.R., Hope B., Iwasaki S., Arinami T., Teasenfitz L., and Uhl G.R. Ann. N.Y. Acad. Sci. 1074 (2006) 514
13. DiMarzo V., Bifulco M., and De Petrocellis L. Nat. Rev. Drug Discov. 3 (2004) 771
14. Salo O.M.H., Savinainen J.R., Parkkari T., Nevalainen T., Lahtela-Kakkonen M., Gynther J., Laitinen J.T., Järvinen T., and Poso A. J. Med. Chem. 49 (2006) 554
15. Beardsley P.M., and Thomas B.F. Behav. Pharmacol. 16 (2005) 275
16. LeFoll B., and Goldberg S.R. J. Pharmacol. Exp. Ther. 312 (2005) 875
17. Tucci S.A., Halford J.C.G., Harrold J.A., and Kirkham T.C. Curr. Med. Chem. 13 (2006) 2669
18. Rinaldi-Carmona M., Barth F., Heaulme M., Shire D., Calandra B., Congy C., Martinez S., Maruani J., Neliat G., and Caput D. FEBS Lett. 350 (1994) 240
19. Pertwee R. Life Sci. 76 (2005) 1307
20. Barth F. Annu. Rep. Med. Chem. 40 (2005) 103
21. Tanda G., and Goldberg S.R. Psychopharmacology 169 (2003) 115
22. Mclaughlin P.J., Winston K., Swezey L., Wisniecki A., Aberman J., Tardif D.J., Betz A.J., Ishiwari K., Makriyannis A., and Salamone J.D. Behav. Pharmacol. 14 (2003) 583
23. Jarbe T.U., DiPatrizio N.V., Li C., and Makriyannis A. Pharmacol. Biochem. Behav. 75 (2003) 809
24. Vivian J.A., Kishioka S., Butelman E.R., Broadbear J., Lee K.O., and Woods J.H. J. Pharmacol. Exp. Ther. 286 (1998) 697
25. Winsauer P.J., Lambert P., and Moerschbaecher J.M. Behav. Pharmacol. 10 (1999) 497
26. Christensen R., Kristensen P.K., Bartels E.M., Biddal H., and Astrup A. Lancet 370 (2007) 1671
27. Thakur G.A., Nikas S.P., Li C., and Makriyannis A. Handb. Exp. Pharmacol. 768 (2005) 209
28. Thomas B.F., Gilliam A.F., Burch D.F., Roche M.J., and Seltzman H.H.J. Pharmacol. Exp. Ther. 285 (1998) 285
29. Hurst D.P., Lynch D.L., Barnett-Norris J., Hyatt S.M., Seltzman H.H., Zhong M., Song Z.-H., Nie J., Lewis D., and Reggio P.H. Mol. Pharmacol. 62 (2002) 1274
30. Shim J.Y., Welsch W.J., Cartier E., Edwards J.L., and Howlett A.C. J. Med. Chem. 45 (2002) 1447
31. Clog P values were calculated using software from Collaborative Drug Discovery, Inc. at www.collabora-tivedrug.com.
32. Lipinski C.A., Lombardo F., Dominy B.W., and Feeny P.J. Adv. Drug Deliv. Rev. 23 (1997) 3
33. Lipinski C.A. J. Pharmacol. Toxicol. Methods 44 (2000) 235
34. Krasinski A., Fokin V.V., and Sharpless K.B. Org. Lett. 6 (2004) 1237
35. Liu Q., and Tor Y. Org. Lett. 5 (2003) 2571
36. Andersen J., Madsen U., Bjorkling F., and Liang X. Synlett 14 (2005) 2209
37. The authors have deposited the crystallographic data for structure 8b with the Cambridge Crystallographic Data Centre (http://www.ccdc.cam.ac.uk/). Deposition number: CCDC 710290.
38. Breivogel C., Sim L., and Childers S. J. Pharmacol. Exp. Ther. 282 (1997) 1632