Design, synthesis and in vitro evaluation of novel uni- and bivalent ligands for the cannabinoid receptor type 1 with variation of spacer length and structure

Bioorganic and Medicinal Chemistry Letters

Volumn 24, Issue 17, 2014, Pages 4209-4214

  Huang, Guozheng ^a,b   Pemp, Daniela ^b   Stadtmüller, Patricia ^a   Nimczick, Martin ^a,b   Heilmann, Jörg ^b   Decker, Michael ^a,b  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Bivalent ligand; Cannabinoid receptor; Rimonabant

Indexed keywords

CANNABINOID 1 RECEPTOR; G PROTEIN COUPLED RECEPTOR; GUANOSINE TRIPHOSPHATASE; LIGAND; RADIOLIGAND; RIMONABANT; AMIDE; AMINE; CANNABINOID RECEPTOR AGONIST; CARBOXYLIC ACID;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; LIGAND BINDING; RECEPTOR AFFINITY; STEADY STATE; STRUCTURE ACTIVITY RELATION; AGONISTS; CHEMISTRY; DOSE RESPONSE; METABOLISM; SYNTHESIS;

AMIDES; AMINES; CANNABINOID RECEPTOR AGONISTS; CARBOXYLIC ACIDS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; HUMANS; LIGANDS; MOLECULAR STRUCTURE; RECEPTOR, CANNABINOID, CB1; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84906936404     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2014.07.038     Document Type: Article

References (39)

1. E.S. Graham, J.C. Ashton, and M. Glass Front. Biosci. (Landmark Ed.) 14 2009 944
2. J.H.M. Lange, and C.G. Kruse Drug Discovery Today 10 2005 693
3. L.D. Petrocellis, M.G. Cascio, and V.D. Marzo Br. J. Pharmacol. 141 2004 765
4. V.D. Marzo, M. Bifulco, and L.D. Petrocellis Nat. Rev. Drug Disc. 3 2004 771
5. T.F. Plasse, R.W. Gorter, S.H. Krasnow, M. Lane, K.V. Shepard, and R.G. Wadleigh Pharmacol. Biochem. Behav. 40 1991 695
6. M. Rinaldi-Carmona, F. Barth, M. Héaulme, D. Shire, B. Calandra, C. Congy, S. Martinez, J. Maruani, G. Néliat, D. Caput, P. Ferrara, P. Soubrié, J.C. Brelière, and G. Le Fur FEBS Lett. 350 1994 240
7. D. Haslam Pract. Diabetes Int. 25 2008 354
8. P.S. Portoghese J. Med. Chem. 44 2001 2259
9. M. Decker, B.S. Fulton, B. Zhang, B.I. Knapp, J.M. Bidlack, and J.L. Neumeyer J. Med. Chem. 52 2009 7389
10. M. Decker, Y.G. Si, B.I. Knapp, J.M. Bidlack, and J.L. Neumeyer J. Med. Chem. 53 2010 402
11. M.R. Del Giudice, A. Borioni, G. Bastanzio, M. Sbraccia, C. Mustazza, and I. Sestili Eur. J. Med. Chem. 46 2011 1207
12. W. Zheng, L. Lei, S. Lalchandani, G. Sun, D.R. Feller, and D.D. Miller Bioorg. Med. Chem. Lett. 10 2000 627
13. P. Karellas, M. McNaughton, S.P. Baker, and P.J. Scammells J. Med. Chem. 51 2008 6128
14. N. Barlow, S.P. Baker, and P.J. Scammells ChemMedChem 8 2013 2036
15. P.C. Meltzer, O. Kryatova, D.-P. Pham-Huu, P. Donovan, and A. Janowsky Bioorg. Med. Chem. 2008 1832 16
16. J. Kühhorn, H. Hübner, and P. Gmeiner J. Med. Chem. 54 2011 4896
17. J. Kühhorn, A. Götz, H. Hübner, D. Thompson, J. Whistler, and P. Gmeiner J. Med. Chem. 54 2011 7911
18. S. Gogoi, S. Biswas, G. Modi, T. Antonio, M.E.A Reith, and A.K. Dutta ACS Med. Chem. Lett. 3 2012 991
19. I. Salama, S. Löber, H. Hübner, and P. Gmeiner Bioorg. Med. Chem. Lett. 24 2014 3753
20. A.P. Tamiz, P. Conti, M. Zhang, K.M. Johnson, and A.P. Kozikowski Bioorg. Med. Chem. Lett. 10 2000 2741
21. O. Russo, M. Berthouze, M. Giner, J.L. Soulier, L. Rivail, S. Sicsic, F. Lezoualc'h, R. Jockers, and I. Berque-Bestel J. Med. Chem. 50 2007 4482
22. W.G. Rajeswaran, Y. Cao, X.P. Huang, M.E. Wroblewski, T. Colclough, S. Lee, F. Liu, P.I. Nagy, J. Ellis, B.A. Levine, K.H. Nocka, and W.S. Messer Jr. J. Med. Chem. 44 2001 4563
23. K. Mohr, J. Schmitz, R. Schrage, C. Tränkle, and U. Holzgrabe Angew. Chem., Int. Ed. 52 2013 508
24. M. Nimczick, D. Pemp, F.H. Darras, X. Chen, J. Heilmann, and M. Decker Bioorg. Med. Chem. 2014 10.1016/j.bmc.2014.06.008
25. J. Shonberg, P.J. Scammells, and B. Capuano ChemMedChem 6 2011 963
26. M. Perez, P.J. Pauwels, C. Fourrier, P. Chopin, J.-P. Valentin, G.W. John, M. Marien, and S. Halazy Bioorg. Med. Chem. Lett. 8 1998 675
27. R.M. Pinder, R.N. Brogden, T.M. Speight, and G.S. Avery Drugs 14 1977 1
28. J.R. Jacoben, S.K. Choi, J. Combs, E.J.L. Fournier, U. Klein, J.W. Pfeiffer, G.R. Thomas, C. Yu, and E.J. Moran Bioorg. Med. Chem. Lett. 22 2012 1213
29. C. Hiller, J. Kühhorn, and P. Gmeiner J. Med. Chem. 56 2013 6542
30. Y. Zhang, A. Gilliam, R. Maitra, M.I. Damaj, J.M. Tajuba, H.H. Seltzman, and B.F. Thomas J. Med. Chem. 53 2010 7048
31. C. Fernández-Fernández, J. Decara, F.J. Bermúdez-Silva, E. Sánchez, P. Morales, M. Gomez-Canas, M. Gómez-Cañas, L.F. Callado, P. Goya, F. Rodríguez de Fonseca, M.I. Martín, J. Fernández-Ruiz, J.J. Meana, and N. Jagerovic Arch. Pharm. 346 2013 171
32. X. Chen, I.G. Tikhonova, and M. Decker Bioorg. Med. Chem. 19 2011 1222
33. T. Birnkammer, A. Spickenreither, I. Brunskole, M. Lopuch, N. Kagermeier, G. Bernhardt, S. Dove, R. Seifert, S. Elz, and A. Buschauer J. Med. Chem. 55 2012 1147
34. F.M. McRobb, I.T. Crosby, E. Yuriev, J.R. Lane, and B. Capuano J. Med. Chem. 55 2012 1622
35. K. Palczewski, T. Kumasaka, T. Hori, C.A. Behnke, H. Motoshima, B.A. Fox, I.L. Trong, D.C. Teller, T. Okada, R.E. Stenkamp, M. Yamamoto, and M. Miyano Science 289 2000 739
36. R. Seifert, and K. Wenzel-Seifert Life Sci. 73 2003 2263
37. S. Geiger, K. Nickl, E.H. Schneider, R. Seifert, and J. Heilmann Naunyn-Schmiedeberg's Arch. Pharmacol. 382 2010 177
38. S. Sutor, J. Heilmann, and R. Seifert J. Pharm. Pharmacol. 63 2011 1043
39. P.S. Portoghese, D.L. Larson, L.M. Sayre, C.B. Yim, G. Ronsisvalle, S.W. Tam, and A.E. Takemori J. Med. Chem. 1986 1855 29