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Volumn 49, Issue 12, 2006, Pages 3509-3519

Mapping the melatonin receptor. 7. Subtype selective ligands based on β-substituted N-acyl-5-methoxytryptamines and β-Substituted N-acyl-5-methoxy-1-methyltryptamines

Author keywords

[No Author keywords available]

Indexed keywords

5 METHOXYTRYPTAMINE; BETA METHYLMELATONIN; BETA,BETA DIMETHYLMELATONIN; MELATONIN 1 RECEPTOR; MELATONIN 2 RECEPTOR; MELATONIN DERIVATIVE; MELATONIN RECEPTOR; N ACYL 5 METHOXY 1 METHYLTRYPTAMINE DERIVATIVE; N ACYL 5 METHOXYTRYPTAMINE DERIVATIVE; N BUTANOYL 5 METHOXY 1 METHYL BETA,BETA TETRAMETHYLENETRYPTAMINE; N BUTANOYL 5 METHOXY 1 METHYL BETA,BETA TRIMETHYLENETRYPTAMINE; UNCLASSIFIED DRUG;

EID: 33745121849     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0512544     Document Type: Article
Times cited : (47)

References (46)
  • 1
    • 22544455330 scopus 로고    scopus 로고
    • Melatonin: Characteristics, concerns and prospects
    • Arendt, J. Melatonin: Characteristics, concerns and prospects. J. Biol. Rhythms 2005, 20, 291-303.
    • (2005) J. Biol. Rhythms , vol.20 , pp. 291-303
    • Arendt, J.1
  • 2
    • 21844433213 scopus 로고    scopus 로고
    • Recent advances in melatonin receptor ligands
    • Zlotos, D. P. Recent advances in melatonin receptor ligands. Arch. Pharm. Chem. Life Sci. 2005, 338, 229-247.
    • (2005) Arch. Pharm. Chem. Life Sci. , vol.338 , pp. 229-247
    • Zlotos, D.P.1
  • 3
    • 0029972613 scopus 로고    scopus 로고
    • Melatonin receptors step into the light: Cloning and classification of subtypes
    • Reppert, S. M.; Weaver, D. R.; Godson, C. Melatonin receptors step into the light: Cloning and classification of subtypes. TiPS 1996, 17, 100-102.
    • (1996) TiPS , vol.17 , pp. 100-102
    • Reppert, S.M.1    Weaver, D.R.2    Godson, C.3
  • 4
    • 0025647581 scopus 로고
    • The distribution of melatonin binding sites in neuroendocrine tissues of the ewe
    • Bittman, E. L.; Weaver, D. R. The distribution of melatonin binding sites in neuroendocrine tissues of the ewe. Biol Reprod. 1990, 43, 986-993.
    • (1990) Biol Reprod. , vol.43 , pp. 986-993
    • Bittman, E.L.1    Weaver, D.R.2
  • 5
    • 0028018966 scopus 로고
    • Cloning and characterisation of a mammalian melatonin receptor that mediates reproductive and circadian responses
    • Reppert, S. M.; Weaver, D. R.; Ebisawa, T. Cloning and characterisation of a mammalian melatonin receptor that mediates reproductive and circadian responses. Neuron 1994, 13, 1177-1185.
    • (1994) Neuron , vol.13 , pp. 1177-1185
    • Reppert, S.M.1    Weaver, D.R.2    Ebisawa, T.3
  • 7
    • 0028868913 scopus 로고
    • Melatonin receptors are for the birds: Molecular analysis of two receptor subtypes differentially expressed in chick brain
    • Reppert, S. M.; Weaver, D. R.; Cassone, V. M.; Godson, C.; Kolakowski, L. F. Melatonin receptors are for the birds: Molecular analysis of two receptor subtypes differentially expressed in chick brain. Neuron 1995, 15, 1003-1015.
    • (1995) Neuron , vol.15 , pp. 1003-1015
    • Reppert, S.M.1    Weaver, D.R.2    Cassone, V.M.3    Godson, C.4    Kolakowski, L.F.5
  • 8
    • 0035371006 scopus 로고    scopus 로고
    • Comparative pharmacological studies of melatonin receptors: MT1, MT2 and MT3/QR2. Tissue distribution of MT3/QR2
    • Nosjean, O.; Nicolas, J. P.; Klupsch, F.; Delagrange, P.; Canet, E.; et al. Comparative pharmacological studies of melatonin receptors: MT1, MT2 and MT3/QR2. Tissue distribution of MT3/QR2. Biochem. Pharmacol. 2001, 61, 1369-1379.
    • (2001) Biochem. Pharmacol. , vol.61 , pp. 1369-1379
    • Nosjean, O.1    Nicolas, J.P.2    Klupsch, F.3    Delagrange, P.4    Canet, E.5
  • 9
    • 0027716547 scopus 로고
    • 2-Substituted 5-methoxy-N-acyltryptamines: Synthesis, binding affinity for the melatonin receptor, and evaluation of biological activity
    • Spadoni. G.; Slankov, B.; Duranti, A.; Biella, G.; Lucini, V.; et al. 2-Substituted 5-methoxy-N-acyltryptamines: Synthesis, binding affinity for the melatonin receptor, and evaluation of biological activity. J. Med. Chem. 1993, 36, 4069-4074.
    • (1993) J. Med. Chem. , vol.36 , pp. 4069-4074
    • Spadoni, G.1    Slankov, B.2    Duranti, A.3    Biella, G.4    Lucini, V.5
  • 10
    • 0028310827 scopus 로고
    • Mapping the melatonin receptor. 1. The 5-methoxyl group of melatonin is not an essential requirement for biological activity
    • Garratt, P. J.; Jones, R.; Rowe, S. J.; Sugden, D. Mapping the melatonin receptor. 1. The 5-methoxyl group of melatonin is not an essential requirement for biological activity. Bioorg. Med. Chem. Lett. 1994, 4, 1555-1558.
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 1555-1558
    • Garratt, P.J.1    Jones, R.2    Rowe, S.J.3    Sugden, D.4
  • 11
    • 0028309734 scopus 로고
    • Mapping the melatonin receptor. 2. Synthesis and biological activity of indole derived melatonin analogues with restricted conformations of the C-3 amidoethane side chain
    • Garratt, P. J.; Vonhoff, S.; Rowe, S. J.; Sugden, D. Mapping the melatonin receptor. 2. Synthesis and biological activity of indole derived melatonin analogues with restricted conformations of the C-3 amidoethane side chain. Bioorg. Med. Chem. Lett. 1994, 4, 1559-1564.
    • (1994) Bioorg. Med. Chem. Lett. , vol.4 , pp. 1559-1564
    • Garratt, P.J.1    Vonhoff, S.2    Rowe, S.J.3    Sugden, D.4
  • 12
    • 0028970287 scopus 로고
    • Mapping the melatonin receptor. 3. Design and synthesis of melatonin agonists and antagonists derived from 2-phenytryptamines
    • Garratt, P. J.; Jones, R.; Tocher, D. A.; Sugden, D. Mapping the melatonin receptor. 3. Design and synthesis of melatonin agonists and antagonists derived from 2-phenytryptamines. J. Med. Chem. 1995, 38, 1132-1139.
    • (1995) J. Med. Chem. , vol.38 , pp. 1132-1139
    • Garratt, P.J.1    Jones, R.2    Tocher, D.A.3    Sugden, D.4
  • 13
    • 0029930956 scopus 로고    scopus 로고
    • Mapping the melatonin receptor. 4. Comparison of the binding affinities of a series of substituted phenylalkylamides
    • Garratt, P. J.; Travard, S.; Vonhoff, S.; Tsotinis, A.; Sugden, D. Mapping the melatonin receptor. 4. Comparison of the binding affinities of a series of substituted phenylalkylamides. J. Med. Chem. 1996, 39, 1797-1805.
    • (1996) J. Med. Chem. , vol.39 , pp. 1797-1805
    • Garratt, P.J.1    Travard, S.2    Vonhoff, S.3    Tsotinis, A.4    Sugden, D.5
  • 14
    • 0032510073 scopus 로고    scopus 로고
    • Mapping the melatonin receptor. 5. Melatonin agonists and antagonists derived from tetrahydrocyclopent[b]indoles, terahydrocarbazoles, and hexahydrocyclohept[b]indoles
    • Davies, D. J.; Garratt, P. J.; Tocher, D. A.; Vonhoff, S.; Davies, J.; et al. Mapping the melatonin receptor. 5. Melatonin agonists and antagonists derived from tetrahydrocyclopent[b]indoles, terahydrocarbazoles, and hexahydrocyclohept[b]indoles. J. Med. Chem. 1998, 41, 451-467.
    • (1998) J. Med. Chem. , vol.41 , pp. 451-467
    • Davies, D.J.1    Garratt, P.J.2    Tocher, D.A.3    Vonhoff, S.4    Davies, J.5
  • 15
    • 0034704888 scopus 로고    scopus 로고
    • Mapping the melatonin receptor. 6. Melatonin agonists and antagonists derived from 6H-isoindolo[2,1-a]indoles, 5,6-dihydroindolo-[2,1-a]isoquinolines, and 6,7-dihydro-5H-benzo[c]azepino[2,1-a]-indoles
    • Faust, R.; Garratt, P. J.; Jones, R.; Yeh, L.-K.; Tsotinis, A.; et al. Mapping the melatonin receptor. 6. Melatonin agonists and antagonists derived from 6H-isoindolo[2,1-a]indoles, 5,6-dihydroindolo-[2,1-a]isoquinolines, and 6,7-dihydro-5H-benzo[c]azepino[2,1-a]-indoles. J. Med. Chem. 2000, 43, 1050-1061.
    • (2000) J. Med. Chem. , vol.43 , pp. 1050-1061
    • Faust, R.1    Garratt, P.J.2    Jones, R.3    Yeh, L.-K.4    Tsotinis, A.5
  • 16
    • 0030000102 scopus 로고    scopus 로고
    • Synthesis and biological activity of conformationally restricted tricyclic analogs of the hormone melatonin
    • Leclerc, V.; Depreux, P.; Lesieur, D.; Caignard, D. H.; Renard, P.; et al. Synthesis and biological activity of conformationally restricted tricyclic analogs of the hormone melatonin. Bioorg. Med. Chem. Lett. 1996, 6, 1071-1076.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 1071-1076
    • Leclerc, V.1    Depreux, P.2    Lesieur, D.3    Caignard, D.H.4    Renard, P.5
  • 17
    • 0030201178 scopus 로고    scopus 로고
    • The high-affinity melatonin binding-site probed with conformationally restricted ligands. 1. Pharmacophore and minireceptor models
    • Jansen, J. M.; Copinga, S.; Gruppen, G.; Molinari, E. J.; Dubocovich, M. L.; et al. The high-affinity melatonin binding-site probed with conformationally restricted ligands. 1. Pharmacophore and minireceptor models. Bioorg. Med. Chem. 1996, 4, 1321-1332.
    • (1996) Bioorg. Med. Chem. , vol.4 , pp. 1321-1332
    • Jansen, J.M.1    Copinga, S.2    Gruppen, G.3    Molinari, E.J.4    Dubocovich, M.L.5
  • 18
    • 0030220790 scopus 로고    scopus 로고
    • The high-affinity melatonin binding site probed with conformationally restricted ligands. 2. Homology modeling of the receptor
    • Grol, C. J.; Jansen, J. M. The high-affinity melatonin binding site probed with conformationally restricted ligands. 2. Homology modeling of the receptor. Bioorg. Med. Chem, 1996, 4, 1333-1339.
    • (1996) Bioorg. Med. Chem , vol.4 , pp. 1333-1339
    • Grol, C.J.1    Jansen, J.M.2
  • 19
    • 9344269392 scopus 로고    scopus 로고
    • Synthesis of 2-amido-2,3-dihydro-1H-phenalene derivatives as new conformationally restricted ligands for melatonin receptors
    • Mathé-Allainmat, M.; Gaudy, F.; Sicsic, S.; Dangy-Caye, A. L.; Shen, S.; et al. Synthesis of 2-amido-2,3-dihydro-1H-phenalene derivatives as new conformationally restricted ligands for melatonin receptors. J. Med. Chem. 1996, 39, 3089-3095.
    • (1996) J. Med. Chem. , vol.39 , pp. 3089-3095
    • Mathé-Allainmat, M.1    Gaudy, F.2    Sicsic, S.3    Dangy-Caye, A.L.4    Shen, S.5
  • 20
    • 0037068497 scopus 로고    scopus 로고
    • Synthesis of a novel series of benzocycloalkene derivatives as melatonin receptor agonists
    • Fukatsu, K.; Uchikawa, O.; Kawada, M.; Yamano, T.; Yamishita, M.; et al. Synthesis of a novel series of benzocycloalkene derivatives as melatonin receptor agonists. J. Med. Chem. 2002, 45, 4212-4221.
    • (2002) J. Med. Chem. , vol.45 , pp. 4212-4221
    • Fukatsu, K.1    Uchikawa, O.2    Kawada, M.3    Yamano, T.4    Yamishita, M.5
  • 21
    • 0348231818 scopus 로고    scopus 로고
    • Binding affinity and biological activity of oxygen and sulfur isosteres at melatonin receptors as a function of their hydrogen bonding capacity
    • Davies, D. J.; Faust, R.; Garratt, P. J.; Marivingt-Mounir, C.; Davidson, K.; et al. Binding affinity and biological activity of oxygen and sulfur isosteres at melatonin receptors as a function of their hydrogen bonding capacity. Bioorg. Chem. 2004, 32, 1-12.
    • (2004) Bioorg. Chem. , vol.32 , pp. 1-12
    • Davies, D.J.1    Faust, R.2    Garratt, P.J.3    Marivingt-Mounir, C.4    Davidson, K.5
  • 22
    • 0029616447 scopus 로고
    • Radioligand binding affinity and biological activity of the enantiomers of a chiral melatonin analogue
    • Sugden, D.; Davies, D.; Garratt, P. J.; Jones, R.; Vonhoff, S. Radioligand binding affinity and biological activity of the enantiomers of a chiral melatonin analogue. Eur. J. Pharmacol. 1995, 287, 239-243.
    • (1995) Eur. J. Pharmacol. , vol.287 , pp. 239-243
    • Sugden, D.1    Davies, D.2    Garratt, P.J.3    Jones, R.4    Vonhoff, S.5
  • 23
    • 0030598632 scopus 로고    scopus 로고
    • A rhodopsin-based model for melatonin recognition at its G protein-coupled receptor
    • Navajas, C.; Kokkola, T.; Poso, A.; Honka, N.; Gynther, J.; et al. A rhodopsin-based model for melatonin recognition at its G protein-coupled receptor. Eur. J. Pharmacol. 1996, 304, 173-183.
    • (1996) Eur. J. Pharmacol. , vol.304 , pp. 173-183
    • Navajas, C.1    Kokkola, T.2    Poso, A.3    Honka, N.4    Gynther, J.5
  • 24
    • 0031052115 scopus 로고    scopus 로고
    • Three-dimensional quantitative structure-activity relationship of melatonin receptor ligands: A comparative molecular field analysis study
    • Sicsic, S.; Serraz, I.; Andrieux, J.; Brémont, B.; Mathé-Allainmat, M.; et al. Three-dimensional quantitative structure-activity relationship of melatonin receptor ligands: A comparative molecular field analysis study. J. Med. Chem. 1997, 40, 739-748.
    • (1997) J. Med. Chem. , vol.40 , pp. 739-748
    • Sicsic, S.1    Serraz, I.2    Andrieux, J.3    Brémont, B.4    Mathé-Allainmat, M.5
  • 26
    • 15644374179 scopus 로고    scopus 로고
    • Melatonin receptor ligands: Synthesis of new melatonin derivatives and comprehensive comparative molecular field analysis (CoMFA) study
    • Mor, M.; Rivara, S.; Silva, C.; Bordi, F.; Plazzi, P. V.; et al. Melatonin receptor ligands: Synthesis of new melatonin derivatives and comprehensive comparative molecular field analysis (CoMFA) study. J. Med. Chem. 1998, 41, 3831-3844.
    • (1998) J. Med. Chem. , vol.41 , pp. 3831-3844
    • Mor, M.1    Rivara, S.2    Silva, C.3    Bordi, F.4    Plazzi, P.V.5
  • 28
    • 0242301704 scopus 로고    scopus 로고
    • Digging deep - Structure-function relationships in the melatonin receptor family
    • Barrett, P.; Conway, S.; Morgan, P. J. Digging deep - structure-function relationships in the melatonin receptor family. J. Pineal Res. 2003, 35, 221-230.
    • (2003) J. Pineal Res. , vol.35 , pp. 221-230
    • Barrett, P.1    Conway, S.2    Morgan, P.J.3
  • 30
    • 0037189910 scopus 로고    scopus 로고
    • Conformational preferences of jet-cooled melatonin: Probing trans-and cis-amide regions of the potential energy surface
    • Florio, G. M.; Christie, R. A.; Jordan, K. D.; Zwier, T. S. Conformational preferences of jet-cooled melatonin: Probing trans-and cis-amide regions of the potential energy surface. J. Am. Chem Soc. 2002, 124, 10236-10247.
    • (2002) J. Am. Chem Soc. , vol.124 , pp. 10236-10247
    • Florio, G.M.1    Christie, R.A.2    Jordan, K.D.3    Zwier, T.S.4
  • 32
    • 0031771553 scopus 로고    scopus 로고
    • Comparison of the structure-activity relationships of melatonin receptor agonists and antagonists: Lengthening the N-acyl side-chain has different effects on potency on Xenopus melanophores
    • Teh, M.-T.; Sugden, D. Comparison of the structure-activity relationships of melatonin receptor agonists and antagonists: lengthening the N-acyl side-chain has different effects on potency on Xenopus melanophores. Naunyn-Schmiedeberg's Arch. Pharmacol. 1998, 358, 522-528.
    • (1998) Naunyn-Schmiedeberg's Arch. Pharmacol. , vol.358 , pp. 522-528
    • Teh, M.-T.1    Sugden, D.2
  • 33
    • 0033367065 scopus 로고    scopus 로고
    • Design of subtype selective receptor agonists and antagonists
    • Sugden, D.; Yeh, L.-K.; Teh, M.-T. Design of subtype selective receptor agonists and antagonists. Reprod. Nutr. Dev. 1999, 39, 335-344.
    • (1999) Reprod. Nutr. Dev. , vol.39 , pp. 335-344
    • Sugden, D.1    Yeh, L.-K.2    Teh, M.-T.3
  • 35
    • 2942607051 scopus 로고    scopus 로고
    • Melatonin receptor signalling: Finding a path through the dark
    • Masana, M. I.; Dubocovich, M. L. Melatonin receptor signalling: finding a path through the dark. Sci. STKE 2001, 6, 107.
    • (2001) Sci. STKE , vol.6 , pp. 107
    • Masana, M.I.1    Dubocovich, M.L.2
  • 40
    • 0024986890 scopus 로고
    • Action of light on frog pigment cells in culture
    • Daniolos, A.; Lerner, A. B.; Lerner, M. R. Action of light on frog pigment cells in culture. Pigment Cell Res. 1990, 3, 38-43.
    • (1990) Pigment Cell Res. , vol.3 , pp. 38-43
    • Daniolos, A.1    Lerner, A.B.2    Lerner, M.R.3
  • 41
    • 0030962477 scopus 로고    scopus 로고
    • Synthesis of 3-amino-2-(3-indolyl)propanol and propanoate derivatives and preliminary cardiovascular evaluation in rats
    • Pérez-Alvarez, V.; Morales-Rios, M. S.; Hong, E.; Joseph-Nathan, P. Synthesis of 3-amino-2-(3-indolyl)propanol and propanoate derivatives and preliminary cardiovascular evaluation in rats. J. Pharm. Pharmacol. 1997, 49, 246-252.
    • (1997) J. Pharm. Pharmacol. , vol.49 , pp. 246-252
    • Pérez-Alvarez, V.1    Morales-Rios, M.S.2    Hong, E.3    Joseph-Nathan, P.4
  • 42
    • 0033050520 scopus 로고    scopus 로고
    • The putative melatonin antagonist GR128107 is a partial agonist on Xenopus laevis melanophores
    • Teh, M.-T.; Sugden, D. The putative melatonin antagonist GR128107 is a partial agonist on Xenopus laevis melanophores. Br. J. Pharmacol. 1999, 126, 1237-1245.
    • (1999) Br. J. Pharmacol. , vol.126 , pp. 1237-1245
    • Teh, M.-T.1    Sugden, D.2
  • 43
    • 0036369308 scopus 로고    scopus 로고
    • Synthesis of N1-phenethyl substituted indole derivatives as new melatoninergic agonists and antagonists
    • Tsotinis, A.; Vlachou, M.; Eleutheriades, A.; Prinea, E.; Ebreo, D.; et al. Synthesis of N1-phenethyl substituted indole derivatives as new melatoninergic agonists and antagonists. Chem. Pharm. Bull. 2002. 50, 31-39.
    • (2002) Chem. Pharm. Bull. , vol.50 , pp. 31-39
    • Tsotinis, A.1    Vlachou, M.2    Eleutheriades, A.3    Prinea, E.4    Ebreo, D.5
  • 44
    • 0347111832 scopus 로고
    • Recherches en série indolique IV. Préparation de dérivés indolyl-3 acétiques
    • Julia, M.; Lenzi, J. Recherches en série indolique IV. Préparation de dérivés indolyl-3 acétiques. Bull. Soc. Chim. Fr. 1962, 1051-1055.
    • (1962) Bull. Soc. Chim. Fr. , pp. 1051-1055
    • Julia, M.1    Lenzi, J.2
  • 45
    • 0029988128 scopus 로고    scopus 로고
    • New indole derivatives as ACAT inhibitors: Synthesis and structure-activity relationships
    • Bellemin, R.; Decerprit, J.; Festal, D. New indole derivatives as ACAT inhibitors: synthesis and structure-activity relationships. Eur. J. Med. Chem. 1996, 31, 123-132.
    • (1996) Eur. J. Med. Chem. , vol.31 , pp. 123-132
    • Bellemin, R.1    Decerprit, J.2    Festal, D.3
  • 46
    • 0035649958 scopus 로고    scopus 로고
    • A new ring-forming methodology for the synthesis of conformationally constrained bioactive molecules
    • Papahatjis, D. P.; Nikas, S.; Tsotinis, A.; Vlachou, M.; Makiyannis, A. A new ring-forming methodology for the synthesis of conformationally constrained bioactive molecules. Chem. Lett. 2001, 30, 192-193.
    • (2001) Chem. Lett. , vol.30 , pp. 192-193
    • Papahatjis, D.P.1    Nikas, S.2    Tsotinis, A.3    Vlachou, M.4    Makiyannis, A.5


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