Indole Melatonin Agonists and Antagonists Derived by Shifting the Melatonin Side Chain from the C-3 to the N-1 or to the C-2 Indole Position

NeuroSignals

Volumn 8, Issue 1-2, 1999, Pages 24-31

  Tarzia, Giorgio ^a   Diamantini, Giuseppe ^a   Spadoni, Gilberto ^a  

^a UNIVERSITY OF URBINO   (Italy)

Author keywords

Agonists; Antagonists; Melatonin analogs

Indexed keywords

HORMONE ANTAGONIST; INDOLE; MELATONIN; MELATONIN RECEPTOR;

ANIMAL TISSUE; NONHUMAN; REVIEW; STRUCTURE ACTIVITY RELATION;

ANIMALS; BRAIN; DRUG DESIGN; HUMANS; INDOLES; KINETICS; MELATONIN; RECEPTORS, CELL SURFACE; RECEPTORS, CYTOPLASMIC AND NUCLEAR; RECEPTORS, MELATONIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033067581     PISSN: 1424862X     EISSN: 14248638     Source Type: Journal    
DOI: 10.1159/000014565     Document Type: Article

References (29)

1. Hagan RM, Oakley NR: Melatonin comes of age? Trends Pharmacol Sci 1995;16:81-83.
2. Morgan PJ, Barrett P, Howell HE, Helliwell R: Melatonin receptors: localization, molecular pharmacology and physiological significance. Neu-rochem Int 1994;24:101-146.
3. Takaki KS, Mahle CD, Watson AJ: Melatonergic ligands: Pharmaceutical development and clinical applications. Curr Pharm Des 1997;3: 429-438.
4. Ebisawa T, Karne S, Lerner MR, Reppert SM: Expression cloning of a high-affinity melatonin receptor from Xenopus dermal melano-phores. Proc Natl Acad Sci USA 1994;91:6133-6137.
5. Reppert SM, Weaver DR, Ebisawa T: Cloning and characterization of a mammalian melatonin receptor that mediates reproductive and circadian responses. Neuron 1994; 13: 1177-1185.
6. Reppert SM, Godson C, Mahle CD, Weaver DR, Slaugenhaupt SA, Gu-sella JF: Molecular characterization of a second melatonin receptor expressed in human retina and brain: The Mel1b melatonin receptor. Proc Natl Acad Sci USA 1995;92:8734-8738.
7. Mazzucchelli C, Pannacci M, Non-no R, Lucini V, Fraschini F, Stankov BM: The melatonin receptor in the human brain: Cloning experiments and distribution studies. Mol Brain Res 1996;39:117-126.
8. Arendt J, Deacon S: Treatment of circadian rhythm disorders. Melatonin. Chronobiol Int 1997; 14:185-204.
9. Duranti E, Stankov B, Spadoni G, Duranti A, Lucini V, Capsoni S, Biella G, Fraschini F: 2-Bromomela-tonin: Synthesis and characterization of a potent melatonin agonist. Life Sci 1992;51:479-485.
10. Spadoni G, Stankov B, Duranti A, Biella G, Lucini V, Salvatori A, Fraschini F: 2-substituted 5-me-thoxy-N-acyltryptamines: Synthesis, binding affinity for the melatonin receptor, and evaluation of the biological activity. J Med Chem 1993;36:4069-4074.
11. Mor M, Rivara S, Silva C, Bordi F, Plazzi PV, Spadoni G, Diamantini G, Balsamini C, Tarzia G, Fraschini F, Lucini V, Nonno R, Stankov BM: Melatonin receptor ligands: Synthesis of new melatonin derivatives and comprehensive CoMFA study. J Med Chem 1998;41:3831-3844.
12. Spadoni G, Balsamini C, Diaman-tini G, Di Giacomo B, Tarzia G, Mor M, Plazzi PV, Rivara S, Lucini V, Nonno R, Pannacci M, Fraschini F, Stankov BM: Conformationally restrained melatonin analogues: Synthesis, binding affinity for the melatonin receptor, evaluation of the biological activity and molecular modeling study. J Med Chem 1997; 40:1990-2002.
13. Sugden D, Chong NWS, Lewis DFV: Structural requirements at the melatonin receptor. Br J Pharmacol 1995;114:618-623.
14. Jansen JM, Copinga S, Gruppen G, Molinari EJ, Dubocovich ML, Grol CJ: The high affinity melatonin binding site probed with conformationally restricted ligands. I. Pharmacophore and minireceptor models. Bioorg Med Chem 1996;4: 1321-1332.
15. Grol CJ, Jansen JM: The high affinity melatonin binding site probed with conformationally restricted ligands. II. Homology modeling of the receptor. Bioorg Med Chem 1996;4: 1333-1339.
16. Sicsic S, Serraz I, Andrieux J, Bre-mont B, Mathe-Allainmat M, Pon-cet A, Shen S, Langlois M: Threedimensional quantitative structure-activity relationship of melatonin receptor ligands: A comparative molecular field analysis study. J Med Chem 1997;40:739-748.
17. Navajas C, Kokkola T, Poso A, Honka N, Gynther J, Laitinen JT: A rhodopsin-based model for melatonin recognition at its G protein-coupled receptor. Eur J Pharmacol 1996;304:173-183.
18. Tarzia G, Diamantini G, Di Giacomo B, Spadoni G, Esposti D, Nonno R, Lucini V, Pannacci M, Fraschini F, Stankov BM: 1-(2-Alkanamido-ethyl)-6-methoxyindole derivatives: A new class of potent indole melatonin analogues. J Med Chem 1997; 40:2003-2010.
19. 3H]dopamine release from retina. Eur J Pharmacol 1984;105:193-194.
20. Dubocovich ML: Luzindole (N-0774): A novel melatonin receptor antagonist. J Pharmacol Exp Ther 1988;246:902-910.
21. Dubocovich ML: Melatonin receptors: Are there multiple subtypes? Trends Pharmacol Sci 1995; 16:5056.
22. Copinga S, Van Brummelen G, Drijfhout WJ, Tepper PG, Grol CJ, Horn AS, Dubocovich ML: Synthesis and pharmacological evaluation of 4-aryl-2-amidotetralins: Nonin-dolic melatonin-receptor agents. Proc Xlllth International Symposium on Medicinal Chemistry, Paris, Sept 1994.
23. Garratt PJ, Jones R, Tocher DA, 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.
24. Guardiola-Lemaitre B, Delagrange P: Melatonin analogues: from pharmacology to clinical application. Eur J Med Chem 1995;30:643s-651s.
25. 1brecombinant subtypes are used to assess the pharmacological profile of the rabbit retina Ml1 presynaptic heteroreceptor. Naunyn-Schmie-deberg’s Arch Pharmacol 1997;355: 365-375.
26. Davies DJ, Garratt PJ, Tocher DA, Vonhoff S, Davies J, Teh M-C, Sugden D: Mapping the melatonin receptor. 5. Melatonin agonists and antagonists derived from tetra-hydrocyclopent[b] indoles, tetrahy-drocarbazoles and hexahydrocyclo-hept[b]indoles. J Med Chem 1998; 41:451-467.
27. 3)al-kyl]indoles as MT1 melatonin receptor partial agonists, antagonists, and putative inverse agonists. J Med Chem 1998;41:3624-3634.
28. 1a receptor following stable transfection into NIH3T3 cells. Br J Pharmacol 1998;124: 485-492.
29. Cozzi B, Stankov B, Viglietti-Panzica C, Capsoni S, Aste N, Lucini V, Fraschini F, Panzica GC: Distribution and characterization of melatonin receptor in the brain of the Japanese quail, Coturnix japonica. Neurosci Lett 1993;150:149-152.