메뉴 건너뛰기




Volumn 56, Issue 20, 2013, Pages 7965-7975

Structure-activity relationship study of indole-2-carboxamides identifies a potent allosteric modulator for the cannabinoid receptor 1 (CB1)

Author keywords

[No Author keywords available]

Indexed keywords

3 BENZYL 5 CHLORO N [4 (PIPERIDIN 1 YL)PHENETHYL] 1H INDOLE 2 CARBOXAMIDE; 4 (1,1 DIMETHYLHEPTYL) 1',2',3',4',5',6' HEXAHYDRO 2,3' DIHYDROXY 6' (3 HYDROXYPROPYL)BIPHENYL; 5 CHLORO 3 (CYCLOHEXYLMETHYL) N [4 (PIPERIDIN 1 YL)PHENETHYL] 1H INDOLE 2 CARBOXAMIDE; 5 CHLORO 3 ETHYL N [4 (PIPERIDIN 1 YL)PHENETHYL]BENZOFURAN 2 CARBOXAMIDE; 5 CHLORO 3 HEPTYL N [4 (PIPERIDIN 1 YL)PHENETHYL] 1H INDOLE 2 CARBOXAMIDE; 5 CHLORO 3 NONYL N [4 (PIPERIDIN 1 YL)PHENETHYL] 1H INDOLE 2 CARBOXAMIDE; 5 CHLORO 3 PENTYL 1H INDOLE 2 CARBOXYLIC ACID [2 (4 PHENOXYPHENYL)ETHYL]AMIDE; 5 CHLORO 3 PENTYL N [4 (PIPERIDIN 1 YL)BENZYL] 1H INDOLE 2 CARBOXAMIDE; 5 CHLORO 3 PENTYL N [4 (PIPERIDIN 1 YL)PHENETHYL] 1H INDOLE 2 CARBOXAMIDE; 5 CHLORO 3 PHENYL N [4 (PIPERIDIN 1 YL)PHENETHYL] 1H INDOLE 2 CARBOXAMIDE; 5 CHLORO N (4 MORPHOLINOPHENETHYL) 3 PENTYL 1H INDOLE 2 CARBOXAMIDE; 5 CHLORO N [1 [4 (DIMETHYLAMINO)PHENYL] 3 HYDROXYPROPAN 2 YL] 3 PENTYL 1H INDOLE 2 CARBOXAMIDE; 5 CHLORO N [4 (DIMETHYLAMINO)PHENETHYL)BENZOFURAN 2 CARBOXAMIDE; 5 CHLORO N [4 (DIMETHYLAMINO)PHENETHYL] 3 ETHYL 1H INDOLE 2 CARBOXAMIDE; 5 CHLORO N [4 (DIMETHYLAMINO)PHENETHYL] 3 ETHYLBENZOFURAN 2 CARBOXAMIDE; 5 CHLORO N [4 (DIMETHYLAMINO)PHENETHYL] 3 PENTYL 1H INDOLE 2 CARBOXAMIDE; 5 CHLORO N [4 (PIPERIDIN 1 YL)PHENETHYL]BENZOFURAN 2 CARBOXAMIDE; CANNABINOID 1 RECEPTOR; CANNABINOID RECEPTOR AFFECTING AGENT; CHLORO 3 ETHYL N [4 (PIPERIDIN 1 YL)PHENETHYL] 1H INDOLE 2 CARBOXAMIDE; COUMARILAMIDE DERIVATIVE; INDOLE 2 CARBOXAMIDE DERIVATIVE; ORG 27569; UNCLASSIFIED DRUG;

EID: 84886571455     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm4009828     Document Type: Article
Times cited : (39)

References (31)
  • 3
    • 0025878961 scopus 로고
    • Molecular cloning of a human cannabinoid receptor which is also expressed in testis
    • Gerard, C. M.; Mollereau, C.; Vassart, G.; Parmentier, M. Molecular cloning of a human cannabinoid receptor which is also expressed in testis Biochem. J. 1991, 279, 129-134
    • (1991) Biochem. J. , vol.279 , pp. 129-134
    • Gerard, C.M.1    Mollereau, C.2    Vassart, G.3    Parmentier, M.4
  • 4
    • 0032879889 scopus 로고    scopus 로고
    • Localization of cannabinoid CB1 receptors in the human anterior eye and retina
    • Straiker, A. J.; Maguire, G.; Mackie, K.; Lindsey, J. Localization of cannabinoid CB1 receptors in the human anterior eye and retina Invest. Ophthalmol. Vis. Sci. 1999, 40, 2442-2448
    • (1999) Invest. Ophthalmol. Vis. Sci. , vol.40 , pp. 2442-2448
    • Straiker, A.J.1    Maguire, G.2    MacKie, K.3    Lindsey, J.4
  • 7
    • 30444457225 scopus 로고    scopus 로고
    • Cannabinoid pharmacology: The first 66 years
    • Pertwee, R. G. Cannabinoid pharmacology: the first 66 years Br. J. Pharmacol. 2006, 147 (Suppl 1) S163-S171
    • (2006) Br. J. Pharmacol. , vol.147 , Issue.SUPPL. 1
    • Pertwee, R.G.1
  • 8
    • 33144480327 scopus 로고    scopus 로고
    • Cannabinoid receptors as therapeutic targets
    • Mackie, K. Cannabinoid receptors as therapeutic targets Annu. Rev. Pharmacol. Toxicol. 2006, 46, 101-122
    • (2006) Annu. Rev. Pharmacol. Toxicol. , vol.46 , pp. 101-122
    • MacKie, K.1
  • 9
    • 56349095425 scopus 로고    scopus 로고
    • Cannabinoid CB1 receptor inhibition decreases vascular smooth muscle migration and proliferation
    • Rajesh, M.; Mukhopadhyay, P.; Hasko, G.; Pacher, P. Cannabinoid CB1 receptor inhibition decreases vascular smooth muscle migration and proliferation Biochem. Biophys. Res. Commun. 2008, 377, 1248-1252
    • (2008) Biochem. Biophys. Res. Commun. , vol.377 , pp. 1248-1252
    • Rajesh, M.1    Mukhopadhyay, P.2    Hasko, G.3    Pacher, P.4
  • 11
    • 0030857066 scopus 로고    scopus 로고
    • Concurrent stimulation of cannabinoid CB1 and dopamine D2 receptors augments cAMP accumulation in striatal neurons: Evidence for a Gs linkage to the CB1 receptor
    • Glass, M.; Felder, C. C. Concurrent stimulation of cannabinoid CB1 and dopamine D2 receptors augments cAMP accumulation in striatal neurons: evidence for a Gs linkage to the CB1 receptor J. Neurosci. 1997, 17, 5327-5333
    • (1997) J. Neurosci. , vol.17 , pp. 5327-5333
    • Glass, M.1    Felder, C.C.2
  • 12
    • 30044435435 scopus 로고    scopus 로고
    • The cannabinoid agonist WIN55,212-2 increases intracellular calcium via CB1 receptor coupling to Gq/11 G proteins
    • Lauckner, J. E.; Hille, B.; Mackie, K. The cannabinoid agonist WIN55,212-2 increases intracellular calcium via CB1 receptor coupling to Gq/11 G proteins Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 19144-19149
    • (2005) Proc. Natl. Acad. Sci. U. S. A. , vol.102 , pp. 19144-19149
    • Lauckner, J.E.1    Hille, B.2    MacKie, K.3
  • 13
    • 75749126604 scopus 로고    scopus 로고
    • Signal transduction of the CB1 cannabinoid receptor
    • Turu, G.; Hunyady, L. Signal transduction of the CB1 cannabinoid receptor J. Mol. Endocrinol. 2010, 44, 75-85
    • (2010) J. Mol. Endocrinol. , vol.44 , pp. 75-85
    • Turu, G.1    Hunyady, L.2
  • 14
  • 15
    • 77950644306 scopus 로고    scopus 로고
    • CB(1) cannabinoid receptors and their associated proteins
    • Howlett, A. C.; Blume, L. C.; Dalton, G. D. CB(1) cannabinoid receptors and their associated proteins Curr. Med. Chem. 2010, 17, 1382-1393
    • (2010) Curr. Med. Chem. , vol.17 , pp. 1382-1393
    • Howlett, A.C.1    Blume, L.C.2    Dalton, G.D.3
  • 16
    • 77952643387 scopus 로고    scopus 로고
    • Cannabinoid CB1 receptor-interacting proteins: Novel targets for central nervous system drug discovery?
    • Smith, T. H.; Sim-Selley, L. J.; Selley, D. E. Cannabinoid CB1 receptor-interacting proteins: novel targets for central nervous system drug discovery? Br. J. Pharmacol. 2010, 160, 454-466
    • (2010) Br. J. Pharmacol. , vol.160 , pp. 454-466
    • Smith, T.H.1    Sim-Selley, L.J.2    Selley, D.E.3
  • 17
    • 0032802188 scopus 로고    scopus 로고
    • Pharmacology of cannabinoid receptor ligands
    • Pertwee, R. G. Pharmacology of cannabinoid receptor ligands Curr. Med. Chem. 1999, 6, 635-664
    • (1999) Curr. Med. Chem. , vol.6 , pp. 635-664
    • Pertwee, R.G.1
  • 18
    • 73549098434 scopus 로고    scopus 로고
    • Ligand- and heterodimer-directed signaling of the CB(1) cannabinoid receptor
    • Hudson, B. D.; Hebert, T. E.; Kelly, M. E. Ligand- and heterodimer-directed signaling of the CB(1) cannabinoid receptor Mol. Pharmacol. 2010, 77, 1-9
    • (2010) Mol. Pharmacol. , vol.77 , pp. 1-9
    • Hudson, B.D.1    Hebert, T.E.2    Kelly, M.E.3
  • 21
    • 67650648706 scopus 로고    scopus 로고
    • Positive allosteric modulation of the human cannabinoid (CB) receptor by RTI-371, a selective inhibitor of the dopamine transporter
    • Navarro, H. A.; Howard, J. L.; Pollard, G. T.; Carroll, F. I. Positive allosteric modulation of the human cannabinoid (CB) receptor by RTI-371, a selective inhibitor of the dopamine transporter Br. J. Pharmacol. 2009, 156, 1178-1184
    • (2009) Br. J. Pharmacol. , vol.156 , pp. 1178-1184
    • Navarro, H.A.1    Howard, J.L.2    Pollard, G.T.3    Carroll, F.I.4
  • 23
    • 84859479825 scopus 로고    scopus 로고
    • Allosteric modulator ORG27569 induces CB1 cannabinoid receptor high affinity agonist binding state, receptor internalization, and Gi protein-independent ERK1/2 kinase activation
    • Ahn, K. H.; Mahmoud, M. M.; Kendall, D. A. Allosteric modulator ORG27569 induces CB1 cannabinoid receptor high affinity agonist binding state, receptor internalization, and Gi protein-independent ERK1/2 kinase activation J. Biol. Chem. 2012, 287, 12070-12082
    • (2012) J. Biol. Chem. , vol.287 , pp. 12070-12082
    • Ahn, K.H.1    Mahmoud, M.M.2    Kendall, D.A.3
  • 24
    • 84874117655 scopus 로고    scopus 로고
    • Profiling two indole-2-carboxamides for allosteric modulation of the CB1 receptor
    • Ahn, K. H.; Mahmoud, M. M.; Samala, S.; Lu, D.; K., D. A. Profiling two indole-2-carboxamides for allosteric modulation of the CB1 receptor J. Neurochem. 2013, 124, 584-589
    • (2013) J. Neurochem. , vol.124 , pp. 584-589
    • Ahn, K.H.1    Mahmoud, M.M.2    Samala, S.3    Lu, D.4
  • 27
    • 0036258990 scopus 로고    scopus 로고
    • G protein-coupled receptor allosterism and complexing
    • Christopoulos, A.; Kenakin, T. G protein-coupled receptor allosterism and complexing Pharmacol. Rev. 2002, 54, 323-374
    • (2002) Pharmacol. Rev. , vol.54 , pp. 323-374
    • Christopoulos, A.1    Kenakin, T.2
  • 28
    • 84866952392 scopus 로고    scopus 로고
    • A key agonist-induced conformational change in the cannabinoid receptor CB1 is blocked by the allosteric ligand Org 27569
    • Fay, J. F.; Farrens, D. L. A key agonist-induced conformational change in the cannabinoid receptor CB1 is blocked by the allosteric ligand Org 27569 J. Biol. Chem. 2012, 287, 33873-33882
    • (2012) J. Biol. Chem. , vol.287 , pp. 33873-33882
    • Fay, J.F.1    Farrens, D.L.2
  • 29
    • 84864462348 scopus 로고    scopus 로고
    • Allosteric modulators of rhodopsin-like G protein-coupled receptors: Opportunities in drug development
    • Muller, C. E.; Schiedel, A. C.; Baqi, Y. Allosteric modulators of rhodopsin-like G protein-coupled receptors: Opportunities in drug development Pharmacol. Ther. 2012, 135, 292-315
    • (2012) Pharmacol. Ther. , vol.135 , pp. 292-315
    • Muller, C.E.1    Schiedel, A.C.2    Baqi, Y.3
  • 30
    • 0023392945 scopus 로고
    • High-efficiency transformation of mammalian cells by plasmid DNA
    • Chen, C.; Okayama, H. High-efficiency transformation of mammalian cells by plasmid DNA Mol. Cell. Biol. 1987, 7, 2745-2752
    • (1987) Mol. Cell. Biol. , vol.7 , pp. 2745-2752
    • Chen, C.1    Okayama, H.2
  • 31
    • 70349320141 scopus 로고    scopus 로고
    • Dual role of the second extracellular loop of the cannabinoid receptor 1: Ligand binding and receptor localization
    • Ahn, K. H.; Bertalovitz, A. C.; Mierke, D. F.; Kendall, D. A. Dual role of the second extracellular loop of the cannabinoid receptor 1: ligand binding and receptor localization Mol. Pharmacol. 2009, 76, 833-842
    • (2009) Mol. Pharmacol. , vol.76 , pp. 833
    • Ahn, K.H.1    Bertalovitz, A.C.2    Mierke, D.F.3    Kendall, D.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.