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Volumn 1, Issue 5, 2009, Pages 947-967

Methylsulfonylpyrazolyl oxadiazoles and thiadiazoles as potent, orally bioavailable cannabinoid-1 receptor antagonists for the treatment of obesity

Author keywords

[No Author keywords available]

Indexed keywords

1,3,4 OXADIAZOLE DERIVATIVE; 1,3,4 THIADIAZOLE DERIVATIVE; 2 [1 (2 CHLOROPHENYL) 5 (4 CHLOROPHENYL) 4 (METHYLSULFONYL) 1H PYRAZOL 3 YL] 5 [1 (TRIFLUOROMETHYL)CYCLOBUTYL] 1,3,4 THIADIAZOLE; 2 [5 (4 BROMOPHENYL) 1 (2 CHLOROPHENYL) 4 (METHYLSULFONYL) 1H PYRAZOL 3 YL] 5 [1 (TRIFLUOROMETHYL)CYCLOBUTYL]1,3,4 THIADIAZOLE; CANNABINOID 1 RECEPTOR; CANNABINOID RECEPTOR ANTAGONIST; UNCLASSIFIED DRUG;

EID: 71749115522     PISSN: 17568919     EISSN: None     Source Type: Journal    
DOI: 10.4155/fmc.09.64     Document Type: Article
Times cited : (5)

References (37)
  • 1
    • 33745807267 scopus 로고    scopus 로고
    • Obesity: The disease
    • Bray GA. Obesity: the disease. J. Med. Chem. 49, 4001-4007 (2006).
    • (2006) J. Med. Chem. , vol.49 , pp. 4001-4007
    • Bray, G.A.1
  • 2
    • 0003615821 scopus 로고    scopus 로고
    • Report of a WHO consultation on obesity
    • WHO, Geneva, Switzerland
    • WHO. Report of a WHO consultation on obesity. Obesity-preventing and managing a global epidemic. Geneva, Switzerland (2000).
    • (2000) Obesity-preventing and Managing A Global Epidemic
  • 3
    • 33745872950 scopus 로고    scopus 로고
    • CB1 cannabinoid receptor antagonists for treatment of obesity and prevention of comorbid metabolic disorders
    • Antel J, Gregory PC, Nordheim, U. CB1 cannabinoid receptor antagonists for treatment of obesity and prevention of comorbid metabolic disorders. J. Med. Chem. 49, 4008-4016 (2006).
    • (2006) J. Med. Chem. , vol.49 , pp. 4008-4016
    • Antel, J.1    Gregory, P.C.2    Nordheim, U.3
  • 6
    • 21344453761 scopus 로고    scopus 로고
    • The endocannabinoid system and the treatment of obesity
    • Pagotto U, Vicennati V, Pasquali, R. The endocannabinoid system and the treatment of obesity. Ann. Med. 37, 270 (2005).
    • (2005) Ann. Med. , vol.37 , pp. 270
    • Pagotto, U.1    Vicennati, V.2    Pasquali, R.3
  • 7
    • 0030870722 scopus 로고    scopus 로고
    • A second endogenous cannabinoid that modulates long-term potentiation
    • Stella N, Schweitzer P, Piomelli D. A second endogenous cannabinoid that modulates long-term potentiation. Nature 388, 773-778 (1997).
    • (1997) Nature , vol.388 , pp. 773-778
    • Stella, N.1    Schweitzer, P.2    Piomelli, D.3
  • 8
    • 16244420759 scopus 로고    scopus 로고
    • Tricyclic pyrazoles part 2: Synthesis and biological evaluation of novel 4,5-dihydro- 1H-benzo[g]indazole-based ligands for cannabinoid receptors
    • Muineddu G, Ruiu S, Mussinu JM et al. Tricyclic pyrazoles part 2: synthesis and biological evaluation of novel 4,5-dihydro- 1H-benzo[g]indazole- based ligands for cannabinoid receptors. Bioorg. Med. Chem. 13, 3309-3320 (2005).
    • (2005) Bioorg. Med. Chem. , vol.13 , pp. 3309-3320
    • Muineddu, G.1    Ruiu, S.2    Mussinu, J.M.3
  • 9
    • 0025325535 scopus 로고
    • Structure of a cannabinoid receptor and functional expression of the cloned cDNA
    • Matsuda LA, Lolait SJ, Brownstein MJ, Young AC, Bonner TI. Structure of a cannabinoid receptor and functional expression of the cloned cDNA. Nature 346, 561-564 (1990).
    • (1990) Nature , vol.346 , pp. 561-564
    • Matsuda, L.A.1    Lolait, S.J.2    Brownstein, M.J.3    Young, A.C.4    Bonner, T.I.5
  • 10
    • 0027515373 scopus 로고
    • Molecular characterization of a peripheral receptor for cannabinoids
    • Munro S, Thomas KL, Abu-Shaar M. Molecular characterization of a peripheral receptor for cannabinoids. Nature 365, 61-65 (1993).
    • (1993) Nature , vol.365 , pp. 61-65
    • Munro, S.1    Thomas, K.L.2    Abu-Shaar, M.3
  • 11
    • 4644262320 scopus 로고    scopus 로고
    • Recent advances in CB1 cannabinoid receptor antagonists
    • Lange JHM, Kruse CG. Recent advances in CB1 cannabinoid receptor antagonists. Curr. Opin. Drug Discov. Dev. 7, 498-506 (2004).
    • (2004) Curr. Opin. Drug Discov. Dev. , vol.7 , pp. 498-506
    • Lange, J.H.M.1    Kruse, C.G.2
  • 12
    • 19444368081 scopus 로고    scopus 로고
    • Medicinal chemistry strategies to CB1 cannabinoid receptor antagonists
    • Lange JHM, Kruse CG. Medicinal chemistry strategies to CB1 cannabinoid receptor antagonists. Drug Discov. Today 10, 693-702 (2005).
    • (2005) Drug Discov. Today , vol.10 , pp. 693-702
    • Lange, J.H.M.1    Kruse, C.G.2
  • 13
    • 33646447652 scopus 로고    scopus 로고
    • CB1 cannabinoid receptor antagonists
    • Barth F. CB1 cannabinoid receptor antagonists. Annu. Rep. Med. Chem. 40, 103-118 (2005).
    • (2005) Annu. Rep. Med. Chem. , vol.40 , pp. 103-118
    • Barth, F.1
  • 15
    • 34247884385 scopus 로고    scopus 로고
    • Scaffold hopping, synthesis and structure-activity relationships of 5,6-diaryl-pyrazine-2-amide derivatives: A novel series of CB1 receptor antagonists
    • Boström J, Berggren K, Greasley P, Wilstermann M. Scaffold hopping, synthesis and structure-activity relationships of 5,6-diaryl-pyrazine-2-amide derivatives: a novel series of CB1 receptor antagonists. Bioorg. Med. Chem. 15, 4077-4084 (2007).
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 4077-4084
    • Boström, J.1    Berggren, K.2    Greasley, P.3    Wilstermann, M.4
  • 16
    • 56749107436 scopus 로고    scopus 로고
    • Biarylpyrazolyl oxadiazole as potent, selective, orally bioavailable cannabinoid-1 receptor antagonists for the treatment of obesit
    • Lee SH, Seo HJ, Lee, SH et al. Biarylpyrazolyl oxadiazole as potent, selective, orally bioavailable cannabinoid-1 receptor antagonists for the treatment of obesity. J. Med. Chem. 51(22), 7216-7233 (2008).
    • (2008) J. Med. Chem. , vol.51 , Issue.22 , pp. 7216-7233
    • Lee, S.H.1    Seo, H.J.2    Lee, S.H.3
  • 17
    • 33845950577 scopus 로고    scopus 로고
    • Discovery of N-[(1S,2S)-3-(4-chlorophenyl)-2-(3- cyanophenyl)-1- methylpropyl]-2-methyl-2- {[5-(trifluoromethyl) pyridin-2-yl]oxy} propanamide (MK-0364), a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity
    • Lin LS, Lanza TJ, Jewell JP et al. Discovery of N-[(1S,2S)-3-(4- chlorophenyl)-2-(3- cyanophenyl)-1-methylpropyl]-2-methyl-2- {[5-(trifluoromethyl) pyridin-2-yl]oxy} propanamide (MK-0364), a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity. J. Med. Chem. 49, 7584-7587 (2006).
    • (2006) J. Med. Chem. , vol.49 , pp. 7584-7587
    • Lin, L.S.1    Lanza, T.J.2    Jewell, J.P.3
  • 18
    • 34547560379 scopus 로고    scopus 로고
    • Catalytic, enantioselective synthesis of taranabant, a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity
    • Chen Cy, Frey LF, Shultz S et al. Catalytic, enantioselective synthesis of taranabant, a novel, acyclic cannabinoid-1 receptor inverse agonist for the treatment of obesity. Org. Process Res. Dev. 11, 616-623 (2007).
    • (2007) Org. Process Res. Dev. , vol.11 , pp. 616-623
    • Cy, C.1    Frey, L.F.2    Shultz, S.3
  • 19
    • 41849121146 scopus 로고    scopus 로고
    • Conformational analysis and receptor docking of N-[(1S,2S)- 3-(4-chlorophenyl)-2-(3-cyanophenyl)-1- methylpropyl]-2-methyl-2-{[5- (trifluoromethyl)pyridin-2-yl]oxy} propanamide (taranabant, MK-0364), a novel, acyclic cannabinoid-1 receptor inverse agonist
    • Lin LS, Ha S, Ball RG et al. Conformational analysis and receptor docking of N-[(1S,2S)- 3-(4-chlorophenyl)-2-(3-cyanophenyl)-1- methylpropyl]-2-methyl- 2-{[5- (trifluoromethyl)pyridin-2-yl]oxy} propanamide (taranabant, MK-0364), a novel, acyclic cannabinoid-1 receptor inverse agonist. J. Med. Chem. 51, 2108-2114 (2008).
    • (2008) J. Med. Chem. , vol.51 , pp. 2108-2114
    • Lin, L.S.1    Ha, S.2    Ball, R.G.3
  • 20
    • 34248532300 scopus 로고    scopus 로고
    • Antiobesity efficacy of a novel cannabinoid-1 receptor inverse agonist, N-[(1S,2S)-3-(4- chlorophenyl)-2-(3-cyanophenyl)-1- methylpropyl]-2-methyl-2- {[5- (trifluoromethyl)pyridin-2-yl]oxy} propanamide (MK-0364), in rodents
    • Fong TM, Guan XM, Marsh DJ et al. Antiobesity efficacy of a novel cannabinoid-1 receptor inverse agonist, N-[(1S,2S)-3-(4- chlorophenyl)-2-(3- cyanophenyl)-1- methylpropyl]-2-methyl-2-{[5- (trifluoromethyl)pyridin-2-yl]oxy} propanamide (MK-0364), in rodents. J. Pharmacol. Exp. Ther. 321, 1013-1022 (2007).
    • (2007) J. Pharmacol. Exp. Ther. , vol.321 , pp. 1013-1022
    • Fong, T.M.1    Guan, X.M.2    Marsh, D.J.3
  • 21
    • 9144260517 scopus 로고    scopus 로고
    • Synthesis, biological properties, and molecular modeling investigations of novel 3,4-diarylpyrazolines as potent and selective CB1 cannabinoid receptor antagonists
    • Lange JH, Coolen HK, van Stuivenberg HH et al. Synthesis, biological properties, and molecular modeling investigations of novel 3,4-diarylpyrazolines as potent and selective CB1 cannabinoid receptor antagonists. J. Med. Chem. 47, 627 (2004).
    • (2004) J. Med. Chem. , vol.47 , pp. 627
    • Lange, J.H.1    Coolen, H.K.2    Van Stuivenberg, H.H.3
  • 22
    • 60549088559 scopus 로고    scopus 로고
    • Discovery of 1-[9-(4-chlorophenyl)-8-(2- chlorophenyl)-9H-purin-6-yl]-4- ethylaminopiperidine-4-carboxylic acid amide hydrochloride (CP-945,598), a novel, potent, and selective cannabinoid type 1 receptor antagonist
    • Griffith DA, Hadcock JR, Balck SC et al. Discovery of 1-[9-(4-chlorophenyl)-8-(2- chlorophenyl)-9H-purin-6-yl]-4- ethylaminopiperidine-4-carboxylic acid amide hydrochloride (CP-945,598), a novel, potent, and selective cannabinoid type 1 receptor antagonist. J. Med. Chem. 52(2), 234-237 (2009).
    • (2009) J. Med. Chem. , vol.52 , Issue.2 , pp. 234-237
    • Griffith, D.A.1    Hadcock, J.R.2    Balck, S.C.3
  • 23
    • 57049102251 scopus 로고    scopus 로고
    • End of the line for cannabinoid receptor 1 as an anti-obesity target?
    • Jones D. End of the line for cannabinoid receptor 1 as an anti-obesity target? Nature Rev. Drug Discov. 7, 961-962 (2008).
    • (2008) Nature Rev .Drug Discov. , vol.7 , pp. 961-962
    • Jones, D.1
  • 24
    • 48249106686 scopus 로고    scopus 로고
    • Cannabinoid CB1 receptor antagonists in therapeutic and structural perspectives
    • Lange JHM, Kruse CG. Cannabinoid CB1 receptor antagonists in therapeutic and structural perspectives. Chem. Rec. 8, 156-168 (2008).
    • (2008) Chem. Rec. , vol.8 , pp. 156-168
    • Lange, J.H.M.1    Kruse, C.G.2
  • 25
    • 0037187367 scopus 로고    scopus 로고
    • Molecular interaction of the antagonist N-(piperidin-1-yl)-5-(4- chlorophenyl)-12,4-dichlorophenyl)-4- methyl-1H-pyrazole-3-carboxamide with the CB1 cannabinoid receptor
    • Shim JY, Welsh WJ, Cartier E, Edwards JL, Howlett AC. molecular interaction of the antagonist N-(piperidin-1-yl)-5-(4- chlorophenyl)-1-(2,4- dichlorophenyl)-4- methyl-1H-pyrazole-3-carboxamide with the CB1 cannabinoid receptor. J. Med. Chem. 45, 1447-1459 (2002).
    • (2002) J. Med. Chem. , vol.45 , pp. 1447-1459
    • Shim, J.Y.1    Welsh, W.J.2    Cartier, E.3    Edwards, J.L.4    Howlett, A.C.5
  • 26
    • 41149148300 scopus 로고    scopus 로고
    • Tetrazole-biarylpyrazole derivatives as cannabinoid CB1 receptor antagonists
    • Kang SY, Lee SH, Seo HJ et al. Tetrazole-biarylpyrazole derivatives as cannabinoid CB1 receptor antagonists. Bioorg. Med. Chem. Lett. 18, 2384-2388 (2008).
    • (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 2384-2388
    • Kang, S.Y.1    Lee, S.H.2    Seo, H.J.3
  • 27
    • 57749098571 scopus 로고    scopus 로고
    • Diarylpyrazolyl oxadiazole and thiadiazole derivatives as cannabinoid CB1 receptor antagonists
    • Kim JY, Seo HJ, Lee SH et al. Diarylpyrazolyl oxadiazole and thiadiazole derivatives as cannabinoid CB1 receptor antagonists. Bioorg. Med. Chem. Lett. 19, 142-145 (2009).
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 142-145
    • Kim, J.Y.1    Seo, H.J.2    Lee, S.H.3
  • 28
    • 61849137327 scopus 로고    scopus 로고
    • Oxadiazolediarylpyrazole 4-carboxamides as cannabinoid CB1 receptor ligands
    • Lee SH, Seo HJ, Kim MJ et al. Oxadiazolediarylpyrazole 4-carboxamides as cannabinoid CB1 receptor ligands. Bioorg. Med. Chem. Lett. 19, 1899-1902 (2009).
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 1899-1902
    • Lee, S.H.1    Seo, H.J.2    Kim, M.J.3
  • 29
    • 0033602129 scopus 로고    scopus 로고
    • Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists
    • Lan R, Liu Q, Fan P et al. Structure-activity relationships of pyrazole derivatives as cannabinoid receptor antagonists. J. Med. Chem. 42, 769-776 (1999).
    • (1999) J. Med. Chem. , vol.42 , pp. 769-776
    • Lan, R.1    Liu, Q.2    Fan, P.3
  • 30
    • 0037434591 scopus 로고    scopus 로고
    • Synthesis, structure-activity relationship, and evaluation of SR141716 analogues: Development of central cannabinoid receptor ligands with lower lipophilicity
    • Katoch-Rouse R, Pavlova OA, Caulder T, Hoffman AF, Mukhin AG, Horti AG. Synthesis, structure-activity relationship, and evaluation of SR141716 analogues: development of central cannabinoid receptor ligands with lower lipophilicity. J. Med. Chem. 46, 642-645 (2003).
    • (2003) J. Med. Chem. , vol.46 , pp. 642-645
    • Katoch-Rouse, R.1    Pavlova, O.A.2    Caulder, T.3    Hoffman, A.F.4    Mukhin, A.G.5    Horti, A.G.6
  • 31
    • 33845555885 scopus 로고
    • A new synthesis of a-keto esters and acids
    • Nimitz JS, Mosher HS. A new synthesis of a-keto esters and acids. J. Org. Chem. 46, 211-213 (1981).
    • (1981) J. Org. Chem. , vol.46 , pp. 211-213
    • Nimitz, J.S.1    Mosher, H.S.2
  • 32
    • 0033574569 scopus 로고    scopus 로고
    • Novel procedure for the synthesis of 1,1 3,4-oxadiazoles from 1,2-diacylhydrazines using polymer-supported Burgess reagent under microwave conditions
    • Brain CT, Paul JM, Loong Y et al. Novel procedure for the synthesis of 1,3,4-oxadiazoles from 1,2-diacylhydrazines using polymer-supported Burgess reagent under microwave conditions. Tetrahedron Lett. 40, 3275-3278 (1999).
    • (1999) Tetrahedron Lett. , vol.40 , pp. 3275-3278
    • Brain, C.T.1    Paul, J.M.2    Loong, Y.3
  • 33
    • 0035103203 scopus 로고    scopus 로고
    • Synthesis of 1,3,4-oxadiazoles using polymer-supported reagents
    • Brain CT, Brunton SA. Synthesis of 1,3,4-oxadiazoles using polymer-supported reagents. Synlett 40(16), 382 (2001).
    • (2001) Synlett , vol.40 , Issue.16 , pp. 382
    • Brain, C.T.1    Brunton, S.A.2
  • 34
    • 0035900367 scopus 로고    scopus 로고
    • Synthesis of 2-alkoxy-substituted thiophenes,1,3-thiazoles, and related S-heterocycles via Lawesson's reagent-mediated cyclization under microwave irradiation: Applications for liquid crystal synthesis
    • Kiryanov AA, Sampson P, Seed AJ. Synthesis of 2-alkoxy-substituted thiophenes, 1,3-thiazoles, and related S-heterocycles via Lawesson's reagent-mediated cyclization under microwave irradiation: applications for liquid crystal synthesis, J. Org. Chem. 66, 7925-7929 (2001).
    • (2001) J. Org. Chem. , vol.66 , pp. 7925-7929
    • Kiryanov, A.A.1    Sampson, P.2    Seed, A.J.3
  • 35
    • 0027379769 scopus 로고
    • Aminoalkylindole binding in rat cerebellum: Selective displacement by natural and synthetic cannabinoids
    • Kuster JE, Stevenson JI, Ward SJ, D'Ambra TE, Haycock DA. Aminoalkylindole binding in rat cerebellum: selective displacement by natural and synthetic cannabinoids. J. Pharmacol. Exp. Ther. 264, 1352-1363 (1993).
    • (1993) J. Pharmacol. Exp. Ther. , vol.264 , pp. 1352-1363
    • Kuster, J.E.1    Stevenson, J.I.2    Ward, S.J.3    D'Ambra, T.E.4    Haycock, D.A.5
  • 36
    • 0037458690 scopus 로고    scopus 로고
    • Antiobesity effects of chronic cannabinoid CB1 receptor antagonist treatment in diet-induced obese mice
    • Hildebrandt AL, Kelly-Sullivan DM, Black SC. Antiobesity effects of chronic cannabinoid CB1 receptor antagonist treatment in diet-induced obese mice. Eur. J. Pharmacol. 462(1-3), 125-132 (2003).
    • (2003) Eur. J. Pharmacol. , vol.462 , Issue.1-3 , pp. 125-132
    • Hildebrandt, A.L.1    Kelly-Sullivan, D.M.2    Black, S.C.3
  • 37
    • 0037716778 scopus 로고    scopus 로고
    • Integrity of extracellular loop 1 of the human cannabinoid receptor 1 is critical for high-affinity binding of the ligand CP55,940 but not SR141716A
    • Murphy JW, Kendall DA. Integrity of extracellular loop 1 of the human cannabinoid receptor 1 is critical for high-affinity binding of the ligand CP55,940 but not SR141716A. Biochem. Pharmacol. 65, 1623-1631 (2003).
    • (2003) Biochem. Pharmacol. , vol.65 , pp. 1623-1631
    • Murphy, J.W.1    Kendall, D.A.2


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