Design, synthesis, and biological evaluation of new 1,8-naphthyridin-4(1H)- on-3-carboxamide and quinolin-4(1H)-on-3-carboxamide derivatives as CB 2 selective agonists

Journal of Medicinal Chemistry

Volumn 49, Issue 20, 2006, Pages 5947-5957

  Manera, Clementina ^a   Benetti, Veronica ^a   Castelli, M Paola ^b   Cavallini, Tiziana ^a   Lazzarotti, Sara ^a   Pibiri, Fabio ^b   Saccomanni, Giuseppe ^a   Tuccinardi, Tiziano ^a   Vannacci, Alfredo ^c   Martinelli, Adriano ^a   Ferrarini, Pier Luigi ^a  

^a UNIVERSITY OF PISA   (Italy)

^b UNIVERSITY OF CAGLIARI   (Italy)

^c UNIVERSITY OF FLORENCE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,8 NAPHTHYRIDIN 4(1H) ON 3 CARBOXAMIDE; 2,3 DIHYDRO 5 METHYL 3 (MORPHOLINOMETHYL) 6 (1 NAPHTHOYL)PYRROLO[1,2,3 DE][1,4]BENZOXAZINE; 4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CANNABINOID RECEPTOR AGONIST; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); HYDROXYL GROUP; N CYCLOHEXYL 7 CHLORO 1 (2 MORPHOLIN 4 YLETHYL)QUINOLIN 4(1H) ON 3 CARBOXAMIDE; QUINOLIN 4(1H) ON 3 CARBOXAMIDE; RADIOLIGAND; SULFUR 35; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BASOPHIL; BRAIN HOMOGENATE; CONTROLLED STUDY; DRUG DESIGN; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; FLOW CYTOMETRY; HUMAN; HUMAN CELL; HYDROGEN BOND; LIGAND BINDING; MALE; MOLECULAR MODEL; MOUSE; NONHUMAN; RECEPTOR AFFINITY; SPLEEN; STRUCTURE ACTIVITY RELATION;

AMIDES; ANIMALS; BASOPHILS; BRAIN; DRUG DESIGN; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); HUMANS; LIGANDS; MALE; MICE; MICE, INBRED DBA; MODELS, MOLECULAR; NAPHTHYRIDINES; PHOSPHORIC DIESTER HYDROLASES; PYROPHOSPHATASES; QUINOLINES; RADIOLIGAND ASSAY; RECEPTOR, CANNABINOID, CB2; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 33749236407     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0603466     Document Type: Article

References (49)

1. Dewick, P. M. Medicinal Natural Products. A Biosynthetic Approach, 2nd ed.; John Wiley & Sons: New York, 2002; pp 86-89.
2. Devane, W. A.; Hanus, L.; Breuer, A.; Pertwee, R. G.; Stevenson, L. A.; Griffin, G.; Gibson, D.; Mandelbaum, A.; Etinger, A.; Mechoulam, R. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 1992, 258, 1946-1949.
3. Sugiura, T.; Kondo, S.; Sukagawa, A.; Nakane, S.; Shinoda, A.; Itoh, K.; Yamashita, A.; Waku, K. 2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain. Biochem. Biophys. Res. Commun. 1995, 215, 89-97.
4. Ueda, N. Endocannabinoid hydrolases. Prostaglandins Other Lipid Mediators 2002, 68-69, 521-534.
5. Dinh, T. P.; Carpenter, D.; Lesile, F. M.; Freund, T. F.; Katona, I.; Sensi, S. L.; Kathuria, S.; Pomelli, D. Brain monoglyceride lipase participating in endocannabinoid inactivation. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 10819-10824.
6. McFarland, M. J.; Porter, A. C.; Rakhshan, F. R.; Rawat, D. S.; Gibbs, R. A.; Barker, E. L. A role for caveolae/lipid rafts in the uptake and recycling of the endogenous cannabinoid Anandamide. J. Biol. Chem. 2004, 279, 41991-41997.
7. Matsuda, L. A.; Lolait, S. J.; Brownstein, M. J.; Young, A. C.; Bonner, T. I. Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 1990, 346, 561-564.
8. Munro, S.; Thomas, K. L.; Abu-Shaar, M. Molecular characterization of a peripheral receptor for cannabinoids. Nature 1993, 365, 61-65.
9. Howlett, A. C.; Barth, F.; Bonner, T. I.; Cabrai, G.; Casellas, P.; Devane, W. A.; Felder, C. C.; Herkenham, M.; Mackie, K.; Martin, B. R.; Mechoulam, R.; Pertwee, R. G. International Union of Pharmacology. XXVII. Classification of cannabinoid receptors. Pharmacol. Rev. 2002, 54, 161-202.
10. Piomelli, D. The molecular logic of endocannabinoid signaling. Nat. Rev. Neurosci. 2003, 4, 873-884.
11. 2 cannabinoid receptor-mediated peripheral antinociception. Pain 2001, 93, 239-245.
12. Di Marzo, V.; Petrocellis, L. D. Plant, synthetic, and endogenous cannabinoids in medicine. Annu. Rev. Med. 2006, 57, 553-574.
13. Ben Amar, M. Cannabinoids in medicine: A review of their therapeutic potential. J. Ethnopharmacol. 2006, 105, 1-25.
14. Pertwee, R. G. Cannabinoid receptor ligands: clinical and neuropharmacological considerations, relevant to future drug discovery and development. Expert Opin. Invest. Drugs 2000, 9, 1553-1571.
15. Rinaldi-Carmona, M.; Barth, F.; Heaulme, M.; Alonso, R.; Shire, D.; Congy, C.; Soubrie, P.; Breliere, J. C.; Le Fur, G. Biochemical and pharmacological characterisation of SR141716A, the first potent and selective brain cannabinoid receptor antagonist. Life Sci. 1995, 56, 1941-1947.
16. 1 receptor antagonist, in diet-induced obese mice. Am. J. Physiol. 2003, 284, R345-R353.
17. Colombo, G.; Agabio, R.; Diaz, G.; Lobina, C.; Reali, R.; Gessa, G. L. Appetite suppression and weight loss after the cannabinoid antagonist SR 141716. Life Sci. 1998, 63, PL113-PL117.
18. 1) receptor antagonist, blocks the motivational and dopamine-releasing effects of nicotine in rats. Behav. Pharmacol. 2002, 13, 451-463.
19. Lambert, D. M.; Fowler, C. J. The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications. J. Med. Chem. 2005, 48, 5059-5087.
20. 2 cannabinoid receptor agonists: pain relief without psychoactive effects? Curr. Opin. Pharmacol. 2003, 3, 62-67.
21. 2 receptor. J. Pharmacol. Exp. Ther. 2001, 296, 420-425.
22. 2, regulates bone mass. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 696-701.
23. 2 cannabinoid receptor. Cancer Res. 2001, 61, 5784-5789.
24. 2 cannabinoid receptors as a novel therapy to treat malignant lymphoblastic disease. Blood 2002, 100, 627-634.
25. Pertwee, R. G. Cannabinoids and multiple sclerosis. Pharmacol. Ther. 2002, 95, 165-174.
26. 2 and abnormal cannabidiol-sensitive receptors. Eur. J. Pharmacol. 2003, 474, 195-198.
27. Stella, N. Cannabinoid signaling in glial cells. Glia 2004, 48, 267-277.
28. 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.
29. Devane, W. A., III; Dysarz, F. A., III; 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.
30. Melvin, L. S.; Milne, G. M.; Johnson, M. R.; Wilken, G. H.; Howlett, A. C. Structure-activity relationships defining the ACD-tricyclic cannabinoids: cannabinoid receptor binding and analgesic activity. Drug Des. Discovery 1995, 13, 155-166.
31. Brizzi, A.; Brizzi, V.; Cascio, M. G.; Bisogno, T.; Sirianni, R.; Di Marzo, V. Design, synthesis, and binding studies of new potent ligands of cannabinoid receptors. J. Med. Chem. 2005, 48, 7343-7350.
32. Barth, F.; Rinaldi-Carmona, M. The development of cannabinoid antagonists. Curr. Med. Chem. 1999, 6, 745-755.
33. Huffman, J. W. Cannabimimetic indoles, pyrroles and indenes. Curr. Med. Chem. 1999, 6, 705-720.
34. 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, 1921-1933.
35. 1 selectivity. Receptor modeling and automated docking analysis. J. Med. Chem. 2006, 49, 984-994.
36. Caliendo, G.; Greco, G.; Greco, P.; Novellino, E.; Perissutti, E.; Santagada, V.; Barbarulo, D.; Esposito, E.; De Blasi, A. Structure-affinity relationship studies on benzotriazole derivatives binding to 5-HT receptor subtypes. Eur. J. Med. Chem. 1996, 31, 207-213.
37. Carboni, S.; Da Settimo, A.; Ferrarini, P. L.; Tonetti, I. Ricerche nel campo delle 1,8-naftiridine e delle1,9,10-antiridine (Research in the field of the 1,8-naphthyridine and the 1,9.10-anthyridine). Gazz. Chim. Ital. 1971, 101, 129-138.
38. Shah, K. J.; Coats, E. A. Design, synthesis, and correlation analysis of 7-substituted 4-hydroxyquinoline-3-carboxylic acids as inhibitors of cellular respiration. J. Med. Chem. 1977, 20, 1001-1006.
39. Rinaldi-Carmona, M.; Barth, F.; Héaulme, M.; Shire, D.; Calandra, B.; Congy, C.; Martinez, S.; Maurani, J.; Neliat, G.; Caput, D.; Ferrara, P.; Soubrié, P.; Breliere, C.; Le Fur, G. SR 141716A, a potent and selective antagonist of the brain cannabinoid receptor. FEBS Lett. 1994, 350, 240-244.
40. Selley, D. E.; Stark, S.; Sim, L. J.; Childers, S. Cannabinoid receptor stimulation of guanosine-5′-O-(3-[35S]thio) triphosphate binding in rat brain membranes. Life Sci. 1996, 59, 659-668.
41. Breivogel, C.; Sim, L.; Childers, S. Regional differences in cannabinoid receptor/G-protein coupling in rat brain. J. Pharmacol. Exp. Ther. 1997, 282, 1632-1642.
42. Vannacci, A.; Zagli, G.; Marzocca, C.; Pierpaoli, S.; Passani, M. B.; Mannaioni, P. F.; Masini, E. Down-regulation by cannabinoids of the immunological activation of human basophils and guinea pig mast cells. Inflammation Res. 2002, 51, S09-S10.
43. Vannacci, A.; Giannini, L.; Passani, M. B.; Di Felice, A.; Pierpaoli, S.; Zagli, G.; Fantappie, O.; Mozzanti, R.; Masini, E.; Mannaioni, P. F. The endocannabinoid 2-arachidonylglycerol decreases the immunological activation of guinea pig mast cells: involvement of nitric oxide and eicosanoids. J. Pharmacol. Exp. Ther. 2004, 311, 256-264.
44. 2 cannabinoid receptors agonists: synthesis, pharmacological properties and molecular modeling. J. Med. Chem. 2006, 49, 70-79.
45. Morris, G. M.; Goodsell, D. S.; Halliday, R. S.; Huey, R.; Hart, W. E.; Belew, R. K.; Olson, A. J. Automated docking using a Lamarckian genetic algorithm and empirical binding free energy function. J. Comput. Chem. 1998, 19, 1639-1662.
46. 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.
47. 50) of an enzyme reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
48. MacroModel, version 8.5; Schrodinger Inc.: New York, 1999.
49. http://www.scripps.edu/~sanner/python/adt.