Novel 4-oxo-1,4-dihydroquinoline-3-carboxamide derivatives as new CB 2 cannabinoid receptors agonists: Synthesis, pharmacological properties and molecular modeling

Journal of Medicinal Chemistry

Volumn 49, Issue 1, 2006, Pages 70-79

  Stern, Eric ^a   Muccioli, Giulio G ^b   Millet, Régis ^a   Goossens, Jean François ^a   Farce, Amaury ^c   Chavatte, Philippe ^c   Poupaert, Jacques H ^b   Lambert, Didier M ^b   Depreux, Patrick ^a   Hénichart, Jean Pierre ^a  

^a Faculté des Sciences Pharmaceutiques et Biologiques Université de Lille   (France)

^b UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

^c UNIV LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE DERIVATIVE; AMIDE; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CANNABINOID 2 RECEPTOR AGONIST; CANNABINOID RECEPTOR AGONIST; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); N 3 (1 PHENYLETHYL) 4 OXO 1 PENTYL 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N 3 [1 (3,5 DIMETHYL)ADAMANTYL] 4 OXO 1 PENTYL 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N3 (1 ADAMANTYL) 4 OXO 1 PENTYL 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; N3 (2 ADAMANTYL) 4 OXO 1 PENTYL 1,4 DIHYDROQUINOLINE 3 CARBOXAMIDE; QUINOLONE DERIVATIVE; SULFUR 35; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING ASSAY; CHO CELL; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR MODEL; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; RECEPTOR AFFINITY; STRUCTURE ANALYSIS;

CRYSTALLOGRAPHY, X-RAY; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; QUINOLONES; RECEPTOR, CANNABINOID, CB1; RECEPTOR, CANNABINOID, CB2; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 30444443786     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm050467q     Document Type: Article

References (60)

1. Gaoni, Y.; Mechoulam, R. Isolation, structure and partial synthesis of an active constituent of hashish. J. Am. Chem. Soc. 1964, 86, 1646-1647.
2. Khanolkar, D. A.; Palmer, S. L.; Makriyannis, A. Molecular probes for the cannabinoid receptors. Chem. Phys. Lipids 2000, 108, 37-52.
3. Devane, W. A.; Dysarz, F. A.; Johnson, M. R.; Melvin, L. S.; Howlett, A. C. Determination and characterization of a cannabinoid receptor in rat brain. Mol. Pharmacol. 1988, 34, 605-613.
4. Munro, S.; Thomas, K. L.; Abu-Shaar, M. Molecular characterization of a peripheral receptor for cannabinoids. Nature 1993, 365, 61-65.
5. Begg, M.; Pacher, P.; Bátkai, S.; Osei-Hyiaman, D.; Offertáler, L.; Mo, F. M.; Liu, J.; Kunos, G. Evidence for novel cannabinoid receptors. Pharmacol. Ther. 2005, 106, 133-145.
6. Howlett, A. C. Cannabinoid inhibition of adenylate cyclase: relative activity of constituents and metabolites of marihuana. Neuropharmacology 1987, 26, 507-512.
7. Mackie, K.; Hille, B. Cannabinoids inhibit N-type calcium channels in neuroblastoma-glioma cells. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 3825-3829.
8. 2+ channel current. Am. J. Physiol. 1999, 276, H2085-2093.
9. Deadwyler, S. A.; Hampson, R. E.; Mu, J.; Whyte, A.; Childers, S. Cannabinoids modulate voltage sensitive potassium A-current in hippocampal neurons via a cAMP-dependent process. J. Pharmacol. Exp. Ther. 1995, 273, 734-743.
10. 1. Biochem. J. 1995, 312, 637-641.
11. Muccioli, G, G.; Lambert, D. M. Current knowledge on the antagonists and inverse agonists of cannabinoid receptors. Curr: Med. Chem. 2005, 12, 1361-1394.
12. Lambert, D. M.; Fowler, C. J. The endocannabinoid system: drug targets, lead compounds and potential therapeutic applications. J. Med. Chem. 2005, 48, 5059-5087.
13. 2 cannabinoid receptor activation produces antinociception by stimulating peripheral release of endogenous opioids. Proc. Natl. Acad. Sci. USA. 2005, 102, 3093-3098.
14. 2 receptor activation inhibits mechanically evoked responses of wide dynamic range dorsal horn neurons in naive rats and in rat models of inflammatory and neuropathic pain. Eur. J. Neurosci. 2004, 20, 2311-2320.
15. 2 receptor and its endogenous ligand 2-arachidonoylglycerol in 12-O-tetradecanoylphorbol-13-acetate-induced acute inflammation in mouse ear. J. Biol. Chem. 2005, 280, 18488-18497.
16. Sarfaraz, S.; Afaq, F.; Adhami, V. M.; Mukhtar, H. Cannabinoid receptor as a novel target for the treatment of prostate cancer. Cancer Res. 2005, 65, 1635-1641.
17. 2 in the liver. Gastroenterologe 2005, 128, 742-755.
18. Franklin, A.; Stella, N. Arachidonylcyclopropylamide increases microglial cell migration through cannabinoid CBi and abnormal-cannabidiol-sensitive receptors. Eur. J. Pharmacol. 2003, 474, 195-198.
19. Stella, N. Cannabinoid signaling in glial cells. Glia 2004, 48, 267-277.
20. Ramirez, B. G.; Blazquez, C.; Gomez del Pulgar, T.; Guzman, M.; de Ceballos, M. L. Prevention of Alzheimer's disease pathology by cannabinoids: neuroprotection mediated by blockade of microglial activation. J. Neurosci. 2005, 25, 1904-1913.
21. 35S]GTPgammaS binding assay: approaches and applications in pharmacology. Life Sci. 2003, 74, 489-508.
22. Di Marzo, V.; Bisogno, T.; De Petrocellis, L.; Melck, D.; Martin, B. R. Cannabimimetic fatty acid derivatives: the anandamide family and other cndocannabinoids. Curr. Med. Chem. 1999, 6, 721-744.
23. Jagerovic, N.; Hernandez-Folgado, L.; Alkorta, I.; Goya, P.; Navarro, M.; Serrano, A.; Rodriguez de Fonseca, F.; Dannert, M. T.; Alsasua, A.; Suardiaz, M.; Pascual, D.; Martin, M. I. Discovery of 5-(4-chlorophenyl )-1 -(2,4-dichlorophenyl)-3-hexyl-1H-1,2,4-triazole. a novel in vivo cannabinoid antagonist containing a 1,2,4-triazole motif. J. Med. Chem. 2004, 47, 2939-2942.
24. 1 cannabinoid receptor antagonists. J. Med. Chem. 2005, 48, 1823-1838.
25. 1 receptor inverse agonists. Bioorg. Med. Chem. Lett. 2005, 15, 1441-1446.
26. 1 cannabinoid receptor ligands and potential antagonists: synthesis, lipophilicity, affinity and molecular modeling. J. Med. Chem. 2002, 45, 1748-1756.
27. 1 cannabinoid receptor ligands: synthesis and pharmacological evaluation. J. Med. Chem. 2005, 48. 2509-2517.
28. 1 inverse agonists. Bioorg. Med. Chem. Lett. 2005, 15, 645-651.
29. 2 receptor. J. Pharmacol. Exp. Ther. 2001, 296, 420-425.
30. Ferrarini, P. L.; Calderone, V.; Cavallini, T.; Manera, C.; Saccomanni, G.; Pani, L.; Ruiu, S.; Gessa, G. L. Synthesis and biological evaluation of 1,8-naphthyridin-4(1H)-on-3-carboxamide derivatives as new ligands of cannabinoid receptors. Bioorg. Med. Chem. 2004, 12, 1-13.
31. 2 receptor inhibitors: identification of a lead and initial SAR studies. Bioorg. Med. Chem. Lett. 2005, 15, 783-786.
32. Pertwee, R. G. Pharmacology of cannabinoid receptor ligands. Curr. Med. Chem. 1999, 6, 635-664.
33. 2 receptor. Eur. J. Pharmacol. 2000, 396, 141-149.
34. 2 receptors suppresses spinal fos protein expression and pain behavior in a rat model of inflammation. Neuroscience 2003, 119, 747-757.
35. 2 cannabinoid receptor-mediated peripheral antinociception. Pain 2001, 93, 239-245.
36. 2 cannabinoid receptors. Chem. Phys. Lipids 2002, 121, 191-200.
37. 2 cannabinoid receptor agonist: pain relict without psychoactive effects? Curr. Opin. Pharmacol. 2003, 3, 62-67.
38. Steffens, S.; Veillard, N. R.; Arnaud, C.; Pelli, G.; Burger, F.; Staub. C.; Zimmer, A.; Frossard, J. L.; Mach, F. Low dose oral cannabinoid therapy reduces progression of atherosclerosis in mice. Nature 2005, 434, 708-709.
39. Huffman, J. W.; Padgett, L. W. Recent Developments in the Medicinal Chemistry of Cannabimetic Indoles. Pyrroles and Indenes. Curr. T. Med. Chem. 2005, 12, 1395-1411.
40. Kanyonyo, M. R.; Govaerts, S. J.; Hermans, E.; Poupaert, J. H.; Lambert, D. M. 3-Alkyl-(5,5′-diphenyl)imidazolidinediones as new cannabinoid receptor ligands, Bioorg. Med. Chem. Lett. 1999, 9, 2233-2236.
41. Gould, R. G.; Jacobs, W. A. The synthesis of certain substituted quinolines and 5,6-benzoquinolines. J. Am. Chem. Soc. 1939, 61, 2890-2895.
42. Price, C. C.; Roberts, R. M. The synthesis of 4-hydroxyquinolines. J. Am. Chem. Soc. 1946, 68, 1204-1208.
43. Leyva, E.; Monreal, E.; Hernandez, A. Synthesis of fluoro-4- hydroxyquinoline-3-carboxylic acids by the Gould-Jacobs reaction. J. Fluorine Chem. 1999, 94, 7-10.
44. Zhang, M. Q.; Levshin, I.; Vanden Berghe, D.; Haemers, A. Synthesis and antibacterial evolution of 1-(4-thiazolylmethyl)- and 7-(4-thiaxolylmethyl) amino-substituted quinolones. Eur. J. Med. Chem. 1991, 26, 331-334.
45. Jung, J.-C.; Jung, Y.-J.; Park, O.-S. Synthesis of 4-hydroxyquinolin- 2(1H)-one analogues and 2-substituted quinolone derivatives. J. Het. Chem. 2001, 38, 61-67.
46. Salmon-Chemin, L.; Lemaire, A.; De Freitas, S.; Déprez, B.; Sergheraert, C.; Davioud-Charvet, E. Parrallel synthesis of a library of 1,4-naphthoquinones and automated screening of potential inhibitors of trypanothione reductase from Trypanosoma cruzi. Bioorg. Med. Chem. Lett. 2000, 10, 631-635.
47. Pop, I. E.; Déprez, B. P.; Tartar, A. L. Versatile acylation of N-nucleophiles using a new polymer-supported 1-hydroxybenzotriazole derivative. J. Org. Chem. 1997, 62, 2594-2603.
48. Govaerts, S. J.; Hermans, E.; Lambert, D. M. Comparison of cannabinoid ligands affinities and efficacies in murine tissues and in transfected cells expressing human recombinant cannabinoid receptors. Eur. J. Pharm. Sci. 2004, 23, 233-243.
49. 2 receptors. Eur. J. Pharmacol. 2004, 495, 43-53.
50. Lu, D.; Meng, Z.; Thakur, G. A.; Fan, P.; Steed, J.; Tartal, C. L.; Hurst, D. P.; Reggio, P. H.; Deschamps, J. R.; Parrish, D. A.; George, C.; Järbe, T. U. C.; Lamb, R. J.; Makriyannis, A. Adamantyl cannabinoids: A novel class of cannabinergic ligands. J. Med. Chem. 2005, 48, 4576-4585.
51. 1 receptor constitutes an agonist/inverse agonist binding domain. J. Med. Chem. 2003, 46, 5139-5152.
52. Bradford, M. M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal. Biochem. 1976, 72, 248-254.
53. SYBYL 6.9.1. Tripos Associates, Inc., 1699 South Hanley Road, St. Louis, MO 63144.
54. Nathans, J.; Hogness, D. S. Isolation, sequence analysis, and intronexon arrangement of the gene encoding bovine rhodopsin. Cell 1983, 34, 807-814.
55. Thompson, J. P.; Higgins, D. G.; Gibson, T. J. ClustalW: improving the sensitivity of progressive sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res. 1994, 22, 4673-4680.
56. Okada, T.; Sugihara, M.; Bondar, A. N.; Elstner, M.; Entel, P.; Buss, V. The retinal conformation and its environment in rhodopsin in light of a new 2.2 A crystal structure. J. Mol. Biol. 2004, 10, 71-83.
57. Petrey, D.; Xiang, Z.; Tang, C. L.; Xie, L.; Gimpelev, M.; Mitros, T.; Soto, C. S.; Goldsmith-Fischman, S.; Kernytsky, A.; Schlessinger, A.; Koh, I. Y. Y.; Alexov, E.; Honig, B. Using multiple structure alignments, fast model building, and energetic analysis in fold recognition and homology modeling. Proteins: Struct., Func. Genet. 2003, 53, 430-435.
58. Clark, M.; Cramer, R. D., III; Van Opdenbosch, N. Validation of the General Purpose Tripos 5.2 Force Field. J. Comput. Chem. 1989, 10, 982-1012.
59. Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking. J. Mol. Biol. 1997, 267, 727-748.
60. Wang, R.; Lai, L.; Wang, S. Further development and validation of empirical scoring functions for structure-based binding affinity prediction. J. Comput.-Aided Mol. Des. 2002, 16, 11-26.