메뉴 건너뛰기




Volumn 40, Issue 13, 1997, Pages 1990-2002

Conformationally restrained melatonin analogues: Synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity, and molecular modeling study

Author keywords

[No Author keywords available]

Indexed keywords

FORSKOLIN; INDOLE; MELATONIN DERIVATIVE;

EID: 7844223548     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960651z     Document Type: Article
Times cited : (80)

References (64)
  • 1
    • 0025758136 scopus 로고
    • Pineal melatonin: Cell biology of its synthesis and of its physiological interactions
    • Reiter, R. J. Pineal melatonin: Cell biology of its synthesis and of its physiological interactions. Endocr. Rev. 1991, 12, 151-180.
    • (1991) Endocr. Rev. , vol.12 , pp. 151-180
    • Reiter, R.J.1
  • 2
    • 0024553018 scopus 로고
    • Effect of melatonin on jet lag after long haul flights
    • (a) Petrie, K.; Conaglen, J. V.; Thompson, L.; Chamberlain, K. Effect of melatonin on jet lag after long haul flights. Br. Med. J. 1989, 298, 705-707.
    • (1989) Br. Med. J. , vol.298 , pp. 705-707
    • Petrie, K.1    Conaglen, J.V.2    Thompson, L.3    Chamberlain, K.4
  • 3
    • 0022996642 scopus 로고
    • Alleviation of jet lag by melatonin: Preliminary results of a controlled double-blind trial
    • (b) Arendt, J.; Aldhous, M.; Marks, V. Alleviation of jet lag by melatonin: preliminary results of a controlled double-blind trial. Annu. Rev. Chronopharmacol. 1986, 3, 49-52.
    • (1986) Annu. Rev. Chronopharmacol. , vol.3 , pp. 49-52
    • Arendt, J.1    Aldhous, M.2    Marks, V.3
  • 5
    • 0028202804 scopus 로고
    • Effect of inducing nocturnal serum melatonin concentrations in daytime on sleep, mood, body temperature, and performance
    • (b) Dollins, A. B.; Zhdanova, I. V.; Wurtman, R. J.; Lynch, H. J.; Deng, M. H. Effect of inducing nocturnal serum melatonin concentrations in daytime on sleep, mood, body temperature, and performance. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 1824-1828.
    • (1994) Proc. Natl. Acad. Sci. U.S.A. , vol.91 , pp. 1824-1828
    • Dollins, A.B.1    Zhdanova, I.V.2    Wurtman, R.J.3    Lynch, H.J.4    Deng, M.H.5
  • 8
    • 0029059197 scopus 로고
    • The pineal gland and melatonin in relation to aging: A summary of the theories and of the data
    • Reiter, R. J. The pineal gland and melatonin in relation to aging: a summary of the theories and of the data. Exp. Gerontol. 1995, 30, 199-212.
    • (1995) Exp. Gerontol. , vol.30 , pp. 199-212
    • Reiter, R.J.1
  • 10
    • 14444277916 scopus 로고
    • Rosenthal, N. E.; Sack, D. A.; Jacobsen, F. M.; James, S. P.; Parry, B. L.; Arendt, J.; Tamarkin, L.; Wehr, T. A. The role of melatonin in seasonal affective disorder (SAD) and phototherapy. Melatonin Hum. Proc. Int. Congr., 1st 1985, 233-241; Chem. Abstr. 1986, 105, 108599c].
    • (1986) Chem. Abstr. , vol.105
  • 11
    • 0027196665 scopus 로고
    • The immunoneuroendocrine role of melatonin
    • (a) Maestroni, G. J. M. The immunoneuroendocrine role of melatonin. J. Pineal Res. 1993, 14, 1-10.
    • (1993) J. Pineal Res. , vol.14 , pp. 1-10
    • Maestroni, G.J.M.1
  • 13
    • 0001330190 scopus 로고
    • The oncostatic and oncomodulatory role of the pineal gland and melatonin
    • (a) Blask, D. E.; Wilson, S. T.; Lemus-Wilson, A. M. The oncostatic and oncomodulatory role of the pineal gland and melatonin. Adv. Pineal Res. 1994, 7, 235-241.
    • (1994) Adv. Pineal Res. , vol.7 , pp. 235-241
    • Blask, D.E.1    Wilson, S.T.2    Lemus-Wilson, A.M.3
  • 14
    • 0029160684 scopus 로고
    • A randomized study of tamoxifen alone versus tamoxifen plus melatonin in estrogen receptor-negative heavily pretreated metastatic breast cancer patients
    • (b) Lissoni, P.; Ardizzoia, A.; Barni, S.; Paolorossi, F.; Tancini, G.; Meregalli, S.; Esposti, D.; Zubelewicz, B.; Braczowski, R. A randomized study of tamoxifen alone versus tamoxifen plus melatonin in estrogen receptor-negative heavily pretreated metastatic breast cancer patients. Oncol. Rep. 1995, 2, 871-873.
    • (1995) Oncol. Rep. , vol.2 , pp. 871-873
    • Lissoni, P.1    Ardizzoia, A.2    Barni, S.3    Paolorossi, F.4    Tancini, G.5    Meregalli, S.6    Esposti, D.7    Zubelewicz, B.8    Braczowski, R.9
  • 15
    • 0028937541 scopus 로고
    • Modulation of cancer endocrine therapy by melatonin: A phase II study of tamoxifen plus melatonin in metastatic breast cancer patients progressing under tamoxifen alone
    • (c) Lissoni, P.; Barni, S.; Meregalli, S.; Fossati, V.; Cazzaniga, M.; Esposti, D.; Tancini, G. Modulation of cancer endocrine therapy by melatonin: A phase II study of tamoxifen plus melatonin in metastatic breast cancer patients progressing under tamoxifen alone. Br. J. Cancer 1995, 71, 854-856.
    • (1995) Br. J. Cancer , vol.71 , pp. 854-856
    • Lissoni, P.1    Barni, S.2    Meregalli, S.3    Fossati, V.4    Cazzaniga, M.5    Esposti, D.6    Tancini, G.7
  • 16
    • 0029972613 scopus 로고    scopus 로고
    • Melatonin receptors step into the light: Cloning and classification of subtypes
    • (a) Reppert, S. M.; Weaver, D. R.; Godson, C. Melatonin receptors step into the light: cloning and classification of subtypes. Trends Pharmacol. Sci. 1996, 17, 100-102.
    • (1996) Trends Pharmacol. Sci. , vol.17 , pp. 100-102
    • Reppert, S.M.1    Weaver, D.R.2    Godson, C.3
  • 17
    • 0028907243 scopus 로고
    • Melatonin receptors: Are there multiple subtypes?
    • (b) Dubocovic, M. L. Melatonin receptors: are there multiple subtypes? Trends Pharmacol. Sci. 1995, 16, 50-56.
    • (1995) Trends Pharmacol. Sci. , vol.16 , pp. 50-56
    • Dubocovic, M.L.1
  • 18
  • 19
    • 0028306136 scopus 로고
    • Expression cloning of a high-affinity melatonin receptor from Xenopus dermal melanophores
    • Ebisawa, T.; Karne, S.; Lerner, M. R.; Reppert, S. M. Expression cloning of a high-affinity melatonin receptor from Xenopus dermal melanophores. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 6133-6137.
    • (1994) Proc. Natl. Acad. Sci. U.S.A. , vol.91 , pp. 6133-6137
    • Ebisawa, T.1    Karne, S.2    Lerner, M.R.3    Reppert, S.M.4
  • 20
    • 0028018966 scopus 로고
    • Cloning and characterization of a mammalian melatonin receptor that mediates reproductive and circadian responses
    • (a) Reppert, S. M.; Weaver, D. R.; Ebisawa, T. Cloning and characterization 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
  • 23
    • 0027489431 scopus 로고
    • Conformational properties of melatonin and two conformationally restricted agonists: A molecular mechanics and NMR spertroscopic study
    • Jansen, J. M.; Karlén, A.; Grol, C. J.; Hacksell, U. Conformational properties of melatonin and two conformationally restricted agonists: a molecular mechanics and NMR spertroscopic study. Drug Des. Discovery 1993, 10, 115-33.
    • (1993) Drug Des. Discovery , vol.10 , pp. 115-133
    • Jansen, J.M.1    Karlén, A.2    Grol, C.J.3    Hacksell, U.4
  • 24
    • 0023809090 scopus 로고
    • 6-Substituted 1,3,4,5-tetrahydrobenz[cd]indol-4-amines: Potent serotonin agonists
    • (a) Flaugh, M. E.; Mullen, D. L.; Fuller, R. W.; Mason, N. R. 6-Substituted 1,3,4,5-tetrahydrobenz[cd]indol-4-amines: Potent serotonin agonists. J. Med. Chem. 1988, 31, 1746-1753.
    • (1988) J. Med. Chem. , vol.31 , pp. 1746-1753
    • Flaugh, M.E.1    Mullen, D.L.2    Fuller, R.W.3    Mason, N.R.4
  • 26
    • 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
    • (a) Garrat, 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
    • Garrat, P.J.1    Vonhoff, S.2    Rowe, S.J.3    Sugden, D.4
  • 28
    • 0027482462 scopus 로고
    • 2-Amido-8-methoxytetralins: A series of nonindolic melatonin-like agents
    • (c) Copinga, S.; Tepper, P. G.; Grol, C. J.; Horn, A. S.; Dubocovich, M. L. 2-Amido-8-methoxytetralins: A series of nonindolic melatonin-like agents. J. Med. Chem. 1993, 36, 2891-2898.
    • (1993) J. Med. Chem. , vol.36 , pp. 2891-2898
    • Copinga, S.1    Tepper, P.G.2    Grol, C.J.3    Horn, A.S.4    Dubocovich, M.L.5
  • 29
    • 0028300079 scopus 로고
    • N-acyl-3-amino-5-methoxychromans: A new series of non-indolic melatonin analogues
    • (d) Sugden, D. N-acyl-3-amino-5-methoxychromans: a new series of non-indolic melatonin analogues. Eur. J. Pharmacol. 1994, 254, 271-75.
    • (1994) Eur. J. Pharmacol. , vol.254 , pp. 271-275
    • Sugden, D.1
  • 30
    • 0030201178 scopus 로고    scopus 로고
    • The high affinity melatonin binding site probed with conformationally restricted ligands-I. Pharmacophore and minireceptor models
    • (e) Jansen, J. M.; Copinga, S.; Gruppen, G.; Molinari, E. J.; Dubocovich, M. L.; Grol, C. J. The high affinity melatonin binding site probed with conformationally restricted ligands-I. Pharmacophore and minireceptor models. Bioorg. Med. Chem. Lett. 1996, 4, 1321-32.
    • (1996) Bioorg. Med. Chem. Lett. , vol.4 , pp. 1321-1332
    • Jansen, J.M.1    Copinga, S.2    Gruppen, G.3    Molinari, E.J.4    Dubocovich, M.L.5    Grol, C.J.6
  • 31
    • 0030220790 scopus 로고    scopus 로고
    • The high affinity melatonin binding site probed with conformationally restricted ligands-II. Homology modeling of the receptor
    • (f) Grol, C. J.; Jansen, J. M. The high affinity melatonin binding site probed with conformationally restricted ligands-II. Homology modeling of the receptor. Bioorg. Med. Chem. Lett. 1996, 4, 1333-39.
    • (1996) Bioorg. Med. Chem. Lett. , vol.4 , pp. 1333-1339
    • Grol, C.J.1    Jansen, J.M.2
  • 32
    • 0028909154 scopus 로고
    • Structural requirements at the melatonin receptor
    • Sugden, D.; Chong N. W. S.; Lewis, D. F. V. Structural requirements at the melatonin receptor. Br. J. Pharmacol. 1995, 114, 618-623.
    • (1995) Br. J. Pharmacol. , vol.114 , pp. 618-623
    • Sugden, D.1    Chong, N.W.S.2    Lewis, D.F.V.3
  • 33
    • 0027548454 scopus 로고
    • A fast new approach to pharmacophore mapping and its application to dopaminergic and benzodiazepine agonists
    • Martin, Y. C.; Bures, M. G.; Danaher, E. A.; De Lazzer, J.; Lico, I.; Pavlik, P. A. A fast new approach to pharmacophore mapping and its application to dopaminergic and benzodiazepine agonists. J. Comput.-Aided Mol. Des. 1993, 7, 83-102.
    • (1993) J. Comput.-Aided Mol. Des. , vol.7 , pp. 83-102
    • Martin, Y.C.1    Bures, M.G.2    Danaher, E.A.3    De Lazzer, J.4    Lico, I.5    Pavlik, P.A.6
  • 35
    • 14444286659 scopus 로고    scopus 로고
    • note
    • 14e reported two pharmacophore models obtained with a different computational method and a different set of compounds.
  • 37
    • 0027716547 scopus 로고
    • 2-substituted 5-methoxy-N-acyltryptamines: Synthesis, binding affinity for the melatonin receptor, and evaluation of the biological activity
    • Spadoni, G.; Stankov, B.; Duranti, A.; Biella, G.; Lucini, V.; Salvatori, A.; Fraschini, F. 2-substituted 5-methoxy-N-acyltryptamines: synthesis, binding affinity for the melatonin receptor, and evaluation of the biological activity. J. Med. Chem. 1993, 36, 4069-4074.
    • (1993) J. Med. Chem. , vol.36 , pp. 4069-4074
    • Spadoni, G.1    Stankov, B.2    Duranti, A.3    Biella, G.4    Lucini, V.5    Salvatori, A.6    Fraschini, F.7
  • 39
    • 0029821888 scopus 로고    scopus 로고
    • Analogues of diverse structure are unable to differentiate native melatonin receptors in the chicken retina, sheep pars tuberalis and Xenopus Melanophores
    • Subsequent to the submission of this work to the journal the binding affinity of compound 4 was reported by the following: Pickering, H.; Sword, S.; Vonhoff, S.; Jones, R.; Sugden, D. Analogues of diverse structure are unable to differentiate native melatonin receptors in the chicken retina, sheep pars tuberalis and Xenopus Melanophores. Br. J. Pharmacol. 1996, 119, 379-387.
    • (1996) Br. J. Pharmacol. , vol.119 , pp. 379-387
    • Pickering, H.1    Sword, S.2    Vonhoff, S.3    Jones, R.4    Sugden, D.5
  • 40
    • 0029616447 scopus 로고
    • Radioligand binding affinity and biological activity of the enantiomers of a chiral melatonin analogue
    • Sugden, D.; Davies, D. J.; Garrat, 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.J.2    Garrat, P.J.3    Jones, R.4    Vonhoff, S.5
  • 41
    • 0001023594 scopus 로고
    • Carboxyl-mediated Pictet-Spengler reaction. Direct synthesis of 1,2,3,4-tetrahydro-β-carbolines from tryptamine-2-carboxylic acids
    • Narayanan, K.; Schindler, L.; Cook, J. M. Carboxyl-mediated Pictet-Spengler reaction. Direct synthesis of 1,2,3,4-tetrahydro-β-carbolines from tryptamine-2-carboxylic acids. J. Org. Chem. 1991, 56, 359-365.
    • (1991) J. Org. Chem. , vol.56 , pp. 359-365
    • Narayanan, K.1    Schindler, L.2    Cook, J.M.3
  • 43
    • 0021671465 scopus 로고
    • Ergoline Synthons. 2. Synthesis of 1,5-Dihydrobenz[cd]indol-4(3H)-ones and 1,3,4,5-Tetrahydrobenz-[cd]indol-4-amines
    • Kruse, L. I.; Meyer, M. D. Ergoline Synthons. 2. Synthesis of 1,5-Dihydrobenz[cd]indol-4(3H)-ones and 1,3,4,5-Tetrahydrobenz-[cd]indol-4-amines. J. Org. Chem. 1984, 49, 4761-4768.
    • (1984) J. Org. Chem. , vol.49 , pp. 4761-4768
    • Kruse, L.I.1    Meyer, M.D.2
  • 44
    • 0021144951 scopus 로고
    • Ergoline Synthons: Synthesis of 3,4-Dihydro-6-methoxybenz[cd]indol-5(1H)-one (6-methoxy-Uhle's ketone) and 3,4-Dihydro-benz[cd]indol-5(1H)-one (Uhle's ketone) via a Novel decarboxylation of indole-2-carboxylates
    • Meyer, M. D.; Kruse, L. I. Ergoline Synthons: Synthesis of 3,4-Dihydro-6-methoxybenz[cd]indol-5(1H)-one (6-methoxy-Uhle's ketone) and 3,4-Dihydro-benz[cd]indol-5(1H)-one (Uhle's ketone) via a Novel decarboxylation of indole-2-carboxylates. J. Org. Chem. 1984, 49, 3195-3199.
    • (1984) J. Org. Chem. , vol.49 , pp. 3195-3199
    • Meyer, M.D.1    Kruse, L.I.2
  • 45
    • 0021130758 scopus 로고
    • Palladium catalyzed reactions in the synthesis of 3- and 4-substituted indoles. Approach to ergot alkaloids
    • Harrinton, P. J.; Hegedus, L. S. Palladium catalyzed reactions in the synthesis of 3- and 4-substituted indoles. Approach to ergot alkaloids. J. Org. Chem. 1984, 49, 2657-2662.
    • (1984) J. Org. Chem. , vol.49 , pp. 2657-2662
    • Harrinton, P.J.1    Hegedus, L.S.2
  • 46
    • 37049107665 scopus 로고
    • Conversion of aldehydes and ketones into nitriles containing an additional carbon atom
    • Orere, D. M.; Reese, C. B. Conversion of aldehydes and ketones into nitriles containing an additional carbon atom. J. Chem. Soc., Chem. Commun. 1977, 280-281.
    • (1977) J. Chem. Soc., Chem. Commun. , pp. 280-281
    • Orere, D.M.1    Reese, C.B.2
  • 48
    • 0027136195 scopus 로고
    • 2,4-Dimethyl-6H-pyrido[3,2-6]carbazole, an isomer of the antitumor alkaloid ellipticine via the Combes-Beyer reaction
    • Alunni-Bistocchi, G.; Orvietani, P.; Bittoun, P.; Ricci, A.; Lescot, E. 2,4-Dimethyl-6H-pyrido[3,2-6]carbazole, an isomer of the antitumor alkaloid ellipticine via the Combes-Beyer reaction. Pharmazie 1993, 48 (11), 817-820.
    • (1993) Pharmazie , vol.48 , Issue.11 , pp. 817-820
    • Alunni-Bistocchi, G.1    Orvietani, P.2    Bittoun, P.3    Ricci, A.4    Lescot, E.5
  • 49
    • 0014516863 scopus 로고
    • Preparation and antiinflammatory properties of some 1-substituted 3-(5-tetrazolylmethyl)indoles and homologs
    • Juby, P. F. ; Hudyma, T. W. Preparation and antiinflammatory properties of some 1-substituted 3-(5-tetrazolylmethyl)indoles and homologs. J. Med. Chem. 1969, 12, 396-401.
    • (1969) J. Med. Chem. , vol.12 , pp. 396-401
    • Juby, P.F.1    Hudyma, T.W.2
  • 50
    • 0028970287 scopus 로고
    • Mapping the melatonin receptor. 3. Design and synthesis of melatonin agonists and antagonists derived from 2-phenyltryptamines
    • Garrat, 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-phenyltryptamines. J. Med. Chem. 1995, 38, 1132-1139.
    • (1995) J. Med. Chem. , vol.38 , pp. 1132-1139
    • Garrat, P.J.1    Jones, R.2    Tocher, D.A.3    Sugden, D.4
  • 51
    • 0028868913 scopus 로고
    • Melatonin receptors are for the birds: Molecular analysis of two receptor subtypes differentially expressed in the chick brain
    • Reppert, S. M.; Weaver, D. R.; Cassone, V. M.; Godson, C.; Kolakowski, L. F. Jr. Melatonin receptors are for the birds: Molecular analysis of two receptor subtypes differentially expressed in the 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 Jr., L.F.5
  • 53
    • 0024472685 scopus 로고
    • Guanine nucleotides regulate the affinity of melatonin receptors on the ovine pars tuberalis
    • Morgan, P. J.; Lawson, W.; Davidson, G.; Howell, H. E. Guanine nucleotides regulate the affinity of melatonin receptors on the ovine pars tuberalis. Neuroendocrinology 1989, 50, 359-362.
    • (1989) Neuroendocrinology , vol.50 , pp. 359-362
    • Morgan, P.J.1    Lawson, W.2    Davidson, G.3    Howell, H.E.4
  • 54
    • 0028054749 scopus 로고
    • Melatonin receptors: Localization, molecular pharmacology and physiological significance
    • Morgan, P. J.; Barret, P.; Howell, H. E.; Helliwell, R. Melatonin receptors: localization, molecular pharmacology and physiological significance. Neurochem. Int. 1994, 24, 101-146.
    • (1994) Neurochem. Int. , vol.24 , pp. 101-146
    • Morgan, P.J.1    Barret, P.2    Howell, H.E.3    Helliwell, R.4
  • 56
    • 0344584211 scopus 로고
    • Reciprocal modulation of agonist and antagonist binding to muscarinic cholinergic receptor by guanine nucleotide
    • Burgisser, E.; De Lean, A.; Lefkowitz, R. J. Reciprocal modulation of agonist and antagonist binding to muscarinic cholinergic receptor by guanine nucleotide. Proc. Natl. Acad. Sci. U.S.A. 1982, 79, 1732-1736.
    • (1982) Proc. Natl. Acad. Sci. U.S.A. , vol.79 , pp. 1732-1736
    • Burgisser, E.1    De Lean, A.2    Lefkowitz, R.J.3
  • 57
    • 0021697164 scopus 로고
    • 2-dopamine receptor of the anterior pituitary gland
    • 2-dopamine receptor of the anterior pituitary gland. Mol. Pharmacol. 1984, 26, 214-227.
    • (1984) Mol. Pharmacol. , vol.26 , pp. 214-227
    • Wregget, K.A.1    De Lean, A.2
  • 58
    • 0026608113 scopus 로고
    • Drug efficacy at guanine nucleotide-binding regulatory protein-linked receptors: Thermodynamic interpretation of negative antagonism and of receptor activity in the absence of ligand
    • Costa, T.; Ogino, Y.; Munson, P. J.; Onaran, H. O.; Rodbard, D. Drug efficacy at guanine nucleotide-binding regulatory protein-linked receptors: Thermodynamic interpretation of negative antagonism and of receptor activity in the absence of ligand. Mol. Pharmacol. 1992, 41, 549-560.
    • (1992) Mol. Pharmacol. , vol.41 , pp. 549-560
    • Costa, T.1    Ogino, Y.2    Munson, P.J.3    Onaran, H.O.4    Rodbard, D.5
  • 61
    • 33847090053 scopus 로고
    • Nitro olefination of indoles and some substituted benzenes with 1-Dimethylamino-2-nitroethylene
    • Büchi, G.; Mak, C. P. Nitro olefination of indoles and some substituted benzenes with 1-Dimethylamino-2-nitroethylene. J. Org. Chem. 1977, 42, 1784-1786.
    • (1977) J. Org. Chem. , vol.42 , pp. 1784-1786
    • Büchi, G.1    Mak, C.P.2
  • 62
    • 0344707332 scopus 로고    scopus 로고
    • Tripos Inc., St. Louis, MO
    • SYBYL 6.3 Theory Manual p. 87, Tripos Inc., St. Louis, MO.
    • SYBYL 6.3 Theory Manual , pp. 87
  • 63
    • 0025979612 scopus 로고
    • Characterization and mapping of melatonin receptors in the brain of three mammalian species: Rabbit, horse and sheep
    • Stankov, B.; Cozzi, B.; Lucini, V.; Fumagalli, P.; Scaglione, F.; Fraschini, F. Characterization and mapping of melatonin receptors in the brain of three mammalian species: rabbit, horse and sheep. Neuroendocrinology 1991, 53, 214-221.
    • (1991) Neuroendocrinology , vol.53 , pp. 214-221
    • Stankov, B.1    Cozzi, B.2    Lucini, V.3    Fumagalli, P.4    Scaglione, F.5    Fraschini, F.6
  • 64
    • 0026589092 scopus 로고
    • Melatonin signal transduction and mechanism of action in the central nervous system: Using the rabbit cortex as a model
    • Stankov, B.; Biella, G.; Panara, C.; Lucini, V.; Capsoni, S.; Fauteck, J.; Cozzi, B.; Fraschini, F. Melatonin signal transduction and mechanism of action in the central nervous system: using the rabbit cortex as a model. Endocrinology 1992, 130, 2152-2159.
    • (1992) Endocrinology , vol.130 , pp. 2152-2159
    • Stankov, B.1    Biella, G.2    Panara, C.3    Lucini, V.4    Capsoni, S.5    Fauteck, J.6    Cozzi, B.7    Fraschini, F.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.