메뉴 건너뛰기




Volumn 54, Issue 8, 2011, Pages 2961-2970

N -(4-cyanotetrahydro-2 H -pyran-4-yl) and N -(1-cyanocyclohexyl) derivatives of 1,5-diarylpyrazole-3-carboxamides showing high affinity for 18 kDa translocator protein and/or cannabinoid receptors

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 BROMOPHENYL) 4 CYANO N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 5 PHENYL 1H PYRAZOLE 3 CARBOXAMIDE; 1 (2 BROMOPHENYL) N (1 CYANOCYCLOHEXYL) 4 METHYL 5 PHENYL 1H PYRAZOLE 3 CARBOXAMIDE; 1 (2 BROMOPHENYL) N (1 CYANOCYCLOHEXYL) 5 (4 METHOXYPHENYL) 4 METHYL 1H PYRAZOLE 3 CARBOXAMIDE; 1 (2 BROMOPHENYL) N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 4 METHYL 5 PHENYL 1H PYRAZOLE 3 CARBOXAMIDE; 1 (2 BROMOPHENYL) N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 5 (3 FLUOROPHENYL) 4 METHYL 1H PYRAZOLE 3 CARBOXAMIDE; 1 (2 BROMOPHENYL) N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 5 (4 FLUOROPHENYL) 4 METHYL 1H PYRAZOLE 3 CARBOXAMIDE; 1 (2 BROMOPHENYL) N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 5 (4 METHOXYPHENYL) 4 METHYL 1H PYRAZOLE 3 CARBOXAMIDE; 1 (2 BROMOPHENYL) N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 5 PHENYL 1H PYRAZOLE 3 CARBOXAMIDE; 1 (2 CHLOROPHENYL) N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 4 METHYL 5 PHENYL 1H PYRAZOLE 3 CARBOXAMIDE; 1 (2 CHLOROPHENYL) N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) N,4 DIMETHYL 5 PHENYL 1H PYRAZOLE 3 CARBOXAMIDE; 1 (3 BROMOPHENYL) N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 4 METHYL 5 PHENYL 1H PYRAZOLE 3 CARBOXAMIDE; 1 (3 BROMOPHENYL) N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 5 (4 METHOXYPHENYL) 4 METHYL 1H PYRAZOLE 3 CARBOXAMIDE; 1 (4 BROMOPHENYL) N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 4 METHYL 5 PHENYL 1H PYRAZOLE 3 CARBOXAMIDE; 1,5 DIARYLPYRAZOLE 3 CARBOXAMIDE DERIVATIVE; 4 BROMO 1 (3 BROMOPHENYL) N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 5 (4 METHOXYPHENYL) 1H PYRAZOLE 3 CARBOXAMIDE; 4 CYANO N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 1 (2 IODOPHENYL) 5 (4 METHOXYPHENYL) 1H PYRAZOLE 3 CARBOXAMIDE; CANNABINOID 1 RECEPTOR; CANNABINOID RECEPTOR; N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 1 (2 FLUOROPHENYL) 4 METHYL 5 PHENYL 1H PYRAZOLE 3 CARBOXAMIDE; N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 1 (2 FLUOROPHENYL) 5 (4 METHOXYPHENYL) 4 METHYL 1H PYRAZOLE 3 CARBOXAMIDE; N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 1 (2 IODOPHENYL) 4 METHYL 5 PHENYL 1H PYRAZOLE 3 CARBOXAMIDE; N (4 CYANOTETRAHYDRO 2H PYRAN 4 YL) 1 (2 PHENYLPHENYL) 4 METHYL 5 PHENYL 1H PYRAZOLE 3 CARBOXAMIDE; RADIOLIGAND; RIMONABANT; UNCLASSIFIED DRUG;

EID: 79955383737     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2000536     Document Type: Article
Times cited : (36)

References (39)
  • 1
    • 0035462779 scopus 로고    scopus 로고
    • Medical use of cannabis through history
    • Lambert, D. M. Medical use of cannabis through history J. Pharm. Belg. 2001, 56, 111-118
    • (2001) J. Pharm. Belg. , vol.56 , pp. 111-118
    • Lambert, D.M.1
  • 2
    • 33947489961 scopus 로고
    • Isolation, structure, and partial synthesis of an active constituent of hashish
    • Gaoni, Y.; Mechoulam, R. Isolation, structure, and partial synthesis of an active constituent of hashish J. Am. Chem. Soc. 1964, 86, 1646-1647
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 1646-1647
    • Gaoni, Y.1    Mechoulam, R.2
  • 4
    • 0027515373 scopus 로고
    • Molecular characterization of a peripheral receptor for cannabinoids
    • DOI 10.1038/365061a0
    • Munro, S.; Thomas, K. L; Abu-Shaar, M. Molecular characterization of a peripheral receptor for cannabinoids Nature 1993, 364, 61-65 (Pubitemid 23305569)
    • (1993) Nature , vol.365 , Issue.6441 , pp. 61-65
    • Munro, S.1    Thomas, K.L.2    Abu-Shaar, M.3
  • 6
    • 0037177601 scopus 로고    scopus 로고
    • Endocannabinoid signaling in the brain
    • Wilson, R.; Nicoll, R. Endocannabinoid signaling in the brain Science 2002, 296, 678-682
    • (2002) Science , vol.296 , pp. 678-682
    • Wilson, R.1    Nicoll, R.2
  • 7
    • 14344259844 scopus 로고    scopus 로고
    • 1 receptor antagonists as promising new medications for drug dependence
    • DOI 10.1124/jpet.104.077974
    • Le Foll, B.; Goldberg, S. R. Cannabinoid CB1 receptor antagonists as promising new medications for drug dependence J. Pharmacol. Exp. Ther. 2005, 312, 875-883 (Pubitemid 40293744)
    • (2005) Journal of Pharmacology and Experimental Therapeutics , vol.312 , Issue.3 , pp. 875-883
    • Le Foll, B.1    Goldberg, S.R.2
  • 8
    • 3042571675 scopus 로고    scopus 로고
    • Cannabinoid receptor antagonists and obesity
    • Black, S. C. Cannabinoid receptor antagonists and obesity Curr. Opin. Invest. Drugs 2004, 5, 389-394
    • (2004) Curr. Opin. Invest. Drugs , vol.5 , pp. 389-394
    • Black, S.C.1
  • 9
    • 37849029289 scopus 로고    scopus 로고
    • A possible role for the endocannabinoid system in the neurobiology of depression
    • Serra, G.; Fratta, W. A possible role for the endocannabinoid system in the neurobiology of depression Clin. Pract. Epidemiol. Mental Health 2007, 3, 25-36
    • (2007) Clin. Pract. Epidemiol. Mental Health , vol.3 , pp. 25-36
    • Serra, G.1    Fratta, W.2
  • 10
    • 0035961131 scopus 로고    scopus 로고
    • 3H]CP-55940 binding in the human central nervous system: Regional specific changes in density of cannabinoid-1 receptors associated with schizophrenia and cannabis use
    • DOI 10.1016/S0306-4522(00)00552-2, PII S0306452200005522
    • 3H]CP-55940 binding in the human central nervous system: regional specific changes in density of cannabinoid-1 receptors associated with schizophrenia and cannabis use Neuroscience 2001, 103, 9-15 (Pubitemid 32304342)
    • (2001) Neuroscience , vol.103 , Issue.1 , pp. 9-15
    • Dean, B.1    Sundram, S.2    Bradbury, R.3    Scarr, E.4    Copolov, D.D.5
  • 11
    • 59649092456 scopus 로고    scopus 로고
    • Development of radioligands for in vivo imaging of type 1 cannabinoid receptors (CB1) in human brain
    • Horti, A. G.; Van Laere, K. Development of radioligands for in vivo imaging of type 1 cannabinoid receptors (CB1) in human brain Curr. Pharm. Des. 2008, 14, 3363-3383
    • (2008) Curr. Pharm. Des. , vol.14 , pp. 3363-3383
    • Horti, A.G.1    Van Laere, K.2
  • 12
    • 0028129936 scopus 로고
    • SR141716A, a potent and selective antagonist of the brain cannabinoid receptor
    • DOI 10.1016/0014-5793(94)00773-X
    • Rinaldi-Carmona, M.; Barth, F.; Héaulme, M.; Shire, D.; Calandra, B.; Congy, C.; Martinez, S.; Maruani, J.; Néliat, G.; Caput, D.; Ferrara, T.; Soubrié, P.; Brelière, J. C.; Le Fur, G. SR141716A, a potent and selective antagonist of the brain cannabinoid receptor FEBS Lett. 1994, 350, 240-244 (Pubitemid 24268029)
    • (1994) FEBS Letters , vol.350 , Issue.2-3 , pp. 240-244
    • Rinaldi-Carmona, M.1
  • 13
    • 19444368081 scopus 로고    scopus 로고
    • 1 cannabinoid receptor antagonists
    • DOI 10.1016/S1359-6446(05)03427-6, PII S1359644605034276
    • 1 cannabinoid receptor antagonists Drug Discovery Today 2005, 10, 693-702 (Pubitemid 40724551)
    • (2005) Drug Discovery Today , vol.10 , Issue.10 , pp. 693-702
    • Lange, J.H.M.1    Kruse, C.G.2
  • 14
    • 0027241271 scopus 로고
    • Positron-emitting radioligands for studies in vivo - Probes for human psychopharmacology
    • Pike, V. W. Positron-emitting radioligands for studies in vivo: probes for human psychopharmacology J. Psychopharmacol. 1993, 7, 139-158 (Pubitemid 23199541)
    • (1993) Journal of Psychopharmacology , vol.7 , Issue.2 , pp. 139-158
    • Pike, V.W.1
  • 15
    • 0344121272 scopus 로고    scopus 로고
    • Determination of lipophilicity and its use as a predictor of blood-brain barrier penetration of molecular imaging agents
    • DOI 10.1016/j.mibio.2003.09.014, PII S1536163203001719
    • Waterhouse, R. N. Determination of lipophilicity and its use as a predictor of blood-brain barrier penetration of molecular imaging agents Mol. Imaging Biol. 2003, 5, 376-389 (Pubitemid 37489828)
    • (2003) Molecular Imaging and Biology , vol.5 , Issue.6 , pp. 376-389
    • Waterhouse, R.N.1
  • 16
    • 0344983883 scopus 로고    scopus 로고
    • Relationships between radiotracer properties and image quality in molecular imaging of the brain with positron emission tomography
    • DOI 10.1016/j.mibio.2003.09.009, PII S1536163203001677
    • Laruelle, M.; Slifstein, M.; Huang, Y. Relationships between radiotracer properties and image quality in molecular imaging of the brain with positron emission tomography Mol. Imaging Biol. 2003, 5, 363-375 (Pubitemid 37489827)
    • (2003) Molecular Imaging and Biology , vol.5 , Issue.6 , pp. 363-375
    • Laruelle, M.1    Slifstein, M.2    Huang, Y.3
  • 17
    • 56549113643 scopus 로고    scopus 로고
    • In vivo site-directed radiotracers; A mini-review
    • Patel, S.; Gibson, R. In vivo site-directed radiotracers; a mini-review Nucl. Med. Biol. 2008, 35, 805-815
    • (2008) Nucl. Med. Biol. , vol.35 , pp. 805-815
    • Patel, S.1    Gibson, R.2
  • 18
    • 67849083569 scopus 로고    scopus 로고
    • PET Radiotracers: Crossing the blood-brain barrier and surviing metabolism
    • Pike, V. W. PET Radiotracers: crossing the blood-brain barrier and surviing metabolism Trends Pharmacol. Sci. 2009, 30, 431-440
    • (2009) Trends Pharmacol. Sci. , vol.30 , pp. 431-440
    • Pike, V.W.1
  • 24
    • 78649496901 scopus 로고    scopus 로고
    • Nitrile-containing pharmaceuticals: Efficacious roles of the nitrile pharmacophore
    • Fleming, F. F.; Yai, L.; Ravikumar, P. C.; Funk, L.; Shook, B. C. Nitrile-containing pharmaceuticals: efficacious roles of the nitrile pharmacophore J. Med. Chem. 2010, 53, 7902-7917
    • (2010) J. Med. Chem. , vol.53 , pp. 7902-7917
    • Fleming, F.F.1    Yai, L.2    Ravikumar, P.C.3    Funk, L.4    Shook, B.C.5
  • 25
    • 15344344375 scopus 로고    scopus 로고
    • In vitro metabolism of diarylpyrazoles, a novel group of cannabinoid receptor ligands
    • DOI 10.1124/dmd.104.001974
    • Zhang, Q.; Ma, P.; Wang, W.; Cole, R. B.; Wang, G. In vitro metabolism of diarylpyrazoles, a novel group of cannabinoid receptor ligands Drug Metab. Dispos. 2005, 33, 508-517 (Pubitemid 40393193)
    • (2005) Drug Metabolism and Disposition , vol.33 , Issue.4 , pp. 508-517
    • Zhang, Q.1    Ma, P.2    Wang, W.3    Cole, R.B.4    Wang, G.5
  • 28
    • 78649320159 scopus 로고    scopus 로고
    • Radiopharmaceutical chemistry for positron emission tomography
    • Li, Z. B.; Conti, P. S. Radiopharmaceutical chemistry for positron emission tomography Adv. Drug Delivery Rev. 2010, 62, 1031-1051
    • (2010) Adv. Drug Delivery Rev. , vol.62 , pp. 1031-1051
    • Li, Z.B.1    Conti, P.S.2
  • 29
    • 0442283586 scopus 로고
    • A versatile new enamine synthesis
    • White, W. A; Weingarten, H. A versatile new enamine synthesis J. Org. Chem. 1967, 32, 213-214
    • (1967) J. Org. Chem. , vol.32 , pp. 213-214
    • White, W.A.1    Weingarten, H.2
  • 30
    • 40949090466 scopus 로고    scopus 로고
    • A facile and regioselective synthesis of rimonabant through an enamine-directed 1,3-dipolar cycloaddition
    • Donohue, S. R.; Halldin, C.; Pike, V. W. A facile and regioselective synthesis of rimonabant through an enamine-directed 1,3-dipolar cycloaddition Tetrahedron Lett. 2008, 49, 2789-2791
    • (2008) Tetrahedron Lett. , vol.49 , pp. 2789-2791
    • Donohue, S.R.1    Halldin, C.2    Pike, V.W.3
  • 31
    • 0001916915 scopus 로고
    • Endogenous and Synthetic Ligands of Mitochondrial Benzodiazepine Receptors: Structure-Affinity Relationships
    • In;, Ed.; Academic Press Ltd.: London,; Chapter 3, pp - 85.
    • Bourguignon, J.-J. Endogenous and Synthetic Ligands of Mitochondrial Benzodiazepine Receptors: Structure-Affinity Relationships. In Peripheral Benzodiazepine Receptors; Giesen-Crouse, E., Ed.; Academic Press Ltd.: London, 1983; Chapter 3, pp 59 - 85.
    • (1983) Peripheral Benzodiazepine Receptors , pp. 59
    • Bourguignon, J.-J.1    Giesen-Crouse, E.2
  • 32
    • 78349311533 scopus 로고    scopus 로고
    • PET tracers for the peripheral benzodiazepine receptor and uses thereof
    • Schweitzer, P. J.; Fallon, B. A.; Mann, J. J.; Kumar, J. S. D. PET tracers for the peripheral benzodiazepine receptor and uses thereof Drug Discovery Today 2010, 15, 933-942
    • (2010) Drug Discovery Today , vol.15 , pp. 933-942
    • Schweitzer, P.J.1    Fallon, B.A.2    Mann, J.J.3    Kumar, J.S.D.4
  • 39
    • 71749107571 scopus 로고    scopus 로고
    • Synthesis and in vitro autoradiographic evaluation of a novel high-affinity radioiodinated ligand for imaging brain cannabinoid subtype-1 receptors
    • Donohue, S. R.; Varnäs, K.; Jia, Z.; Gulyás, B.; Pike, V. W.; Halldin, C. Synthesis and in vitro autoradiographic evaluation of a novel high-affinity radioiodinated ligand for imaging brain cannabinoid subtype-1 receptors Bioorg. Med. Chem. Lett. 2009, 19, 6209-6212
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 6209-6212
    • Donohue, S.R.1    Varnäs, K.2    Jia, Z.3    Gulyás, B.4    Pike, V.W.5    Halldin, C.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.