Triaryl bis-sulfones as a new class of cannabinoid CB2 receptor inhibitors: Identification of a lead and initial SAR studies

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 3, 2005, Pages 783-786

  Lavey, Brian J ^a   Kozlowski, Joseph A ^a   Hipkin, R William ^a   Gonsiorek, Waldemar ^a   Lundell, Daniel J ^a   Piwinski, John J ^a   Narula, Satwant ^a   Lunn, Charles A ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CANNABINOID RECEPTOR ANTAGONIST; SULFONAMIDE; UREA DERIVATIVE;

ANIMAL CELL; ARTICLE; CELL MEMBRANE; CONTROLLED STUDY; HUMAN; HUMAN CELL; LIGAND BINDING; MEMBRANE TRANSPORT; NONHUMAN; RAT; RECEPTOR BINDING; STRUCTURE ACTIVITY RELATION;

AMIDES; CANNABINOIDS; CELL MEMBRANE; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); HUMANS; LIGANDS; RECEPTOR, CANNABINOID, CB2; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES; SULFONES; UREA;

EID: 12444303171     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.11.007     Document Type: Article

References (32)

1. For reviews on cannabinoid biology, see S.J. Watson, J.A. Benson Jr., and J.E. Joy Arch. Gen. Psychiatry 57 2000 547
2. A. Goutopoulos, and A. Makriyannis Pharmacol. Ther. 95 2002 103
3. for reviews discussing immune modulation by cannabinoid ligands see: T.W. Klein, C. Newton, K. Larsen, L. Lu, I. Perkins, L. Nong, and H. Friedman J. Leukoc. Biol. October 2003 74
4. R.G. Pertwee Exp. Opin. Invest. Drugs 9 2000 1553
5. For a review, see R.G. Pertwee Pharmacol. Ther. 74 1997 129
6. S.R. Smith, G. Denhardt, and C. Terminelli Eur. J. Pharmacol. 432 2001 107
7. S.R. Smith, C. Terminelli, and G. Denhardt Eur. J. Pharmacol. 425 2001 73
8. S.R. Smith, C. Terminelli, and G. Denhardt J. Pharmacol. Exp. Ther. 293 2000 136
9. S. Munro, K.L. Thomas, and M. Abu-Shaar Nature 365 1993 61
10. P. Carayon, J. Marchand, D. Dussossoy, J.M. Derocq, O. Jbilo, A. Bord, M. Bouaboula, S. Galiegue, P. Mondiere, G. Penarier, G.L. Fur, T. Defrance, and P. Casellas Blood 92 1998 3605
11. P. Sacerdote, P. Massi, A.E. Panerai, and D. Parolaro J. Neuroimmunol. 109 2000 155
12. K.L. McCoy, M. Matveyeva, S.J. Carlisle, and G.A. Cabral J. Pharmacol. Exp. Ther. 289 1999 1620
13. L.X. Zhu, S. Sharma, M. Stolina, B. Gardner, M.D. Roth, D.P. Tashkin, and S.M. Dubinett J. Immunol. 165 2000 373
14. R. Sancho, M.A. Calzado, V. DiMarzo, G. Appendino, and E. Munoz Mol. Pharmacol. 63 2003 429
15. For a review, see A.C. Howlett, F. Barth, T.I. Bonner, G. Cabral, P. Casellas, W.A. Devane, C.C. Felder, M. Herkenham, K. Mackie, B.R. Martin, R. Mechoulam, and R.G. Pertwee Pharmacol. Rev. 54 2002 161
16. V.M. Showalter, D.R. Compton, B.R. Martin, and M.E. Abood J. Pharmacol. Exp. Ther. 278 1996 989
17. J.W. Huffman Curr. Pharm. Des. 6 2000 1323
18. R.A. Ross, H.C. Brockie, L.A. Stevenson, V.L. Murphy, F. Templeton, A. Makriyannis, and R.G. Pertwee Br. J. Pharmacol. 126 1999 665
19. M.R. Johnson, and L.S. Melvin R. Mechoulam Cannabinoids as Therapeutic Agents 1986 CRC Boca Raton 121 145
20. R. Pertwee, G. Griffin, S. Fernando, X. Li, A. Hill, and A. Makriyannis Life Sci. 56 1995 1949
21. J.W. Huffman Curr. Med. Chem. 6 1999 705
22. W.A. Devane, L. Hanus, A. Breuer, R.G. Pertwee, L.A. Stevenson, G. Griffin, D. Gibson, A. Mandelbaum, A. Etinger, and R. Mechoulam Science 258 1992 1946
23. Reviewed in S.L. Palmer, A.D. Khanolkar, and A. Makriyannis Curr. Pharm. Des. 6 2000 1381
24. M. Rinaldi-Carmona, F. Barth, M. Heaulme, D. Shire, B. Calandra, C. Congy, S. Martinez, J. Maruani, G. Neliat, and D. Caput FEBS Lett. 350 1994 240
25. M. Rinaldi-Carmona, F. Barth, J. Millan, J.M. Derocq, P. Casellas, C. Congy, D. Oustric, M. Sarran, M. Bouaboula, B. Calandra, M. Portier, D. Shire, J.C. Breliere, and G.L. Le Fur J. Pharmacol. Exp. Ther. 284 1998 644
26. S.P. Vickers, L.J. Webster, A. Wyatt, C.T. Dourish, and G.A. Kennett Psychopharmacol. 167 2003 103
27. i data will refer to the human CB2 receptor
28. i values, see: Kozlowski, J. A.; Shih, N. -Y.; Lavey, B. J.; Rizvi, R. K.; Shankar, B. P; Spitler, J. M.; Tong, L.; Wolin, R.; Wong, M. K. World Patent WO02062750
29. 2, and 0.2% (w/v) BSA (Factor V, lipid free), pH 7.4 supplemented with 2.5 μM GDP. Following incubation for 30 min at 30°C the reaction was terminated by rapid filtration through the microfiltration plates. The filters were washed 10 times at room temperature with 20 mM HEPES and 10 mM sodium pyrophosphate, and membrane-bound radioactivity was measured by liquid scintillation. Nonlinear regression analysis of the data was performed with Prism 2.0b (GraphPad, San Diego, CA). Additional information may be found in: W. Gonsiorek, C. Lunn, X. Fan, S. Narula, D. Lundell, and R.W. Hipkin Mol. Pharmacol. 57 2000 1045
30. H. Iwamura, H. Suzuki, Y. Ueda, T. Kaya, and T. Inaba J. Pharmacol. Exp. Ther. 296 2001 420
31. A.G. Nackley, A. Makriyannis, and A.G. Hohmann Neuroscience 119 2003 747
32. A.G. Nackley, R.L. Suplita II, and A.G. Hohmann Neuroscience 117 2003 659