Synthesis of 2-amido-2,3-dihydro-1H-phenalene derivatives as new conformationally restricted ligands for melatonin receptors

Journal of Medicinal Chemistry

Volumn 39, Issue 16, 1996, Pages 3089-3095

  Mathé Allainmat, Monique ^a   Gaudy, Florence ^a   Sicsic, Sames ^a   Dangy Caye, Anne Laure ^a   Shen, Shuren ^a   Brémont, Béatrice ^a   Benatalah, Zohra ^a   Langlois, Michel ^a   Renard, Pierre ^b   Delagrange, Philippe ^c  

^a UNIVERSITÉ PARIS SACLAY   (France)

^b ADIR   (France)

^c INSTITUT DE RECHERCHES INTERNATIONALES SERVIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

4 METHOXY 2 PROPIONAMIDO 2,3 DIHYDRO 1H PHENALENE; MELATONIN RECEPTOR; PROPIONAMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BRAIN MEMBRANE; DRUG BINDING SITE; DRUG CONFORMATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; MELANOCYTE; MELANOSOME; NONHUMAN; RECEPTOR AFFINITY; XENOPUS LAEVIS;

AMIDES; ANIMALS; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MELANOCYTES; MELANOPHORES; MELATONIN; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; POLYCYCLIC COMPOUNDS; RECEPTORS, CELL SURFACE; RECEPTORS, MELATONIN; STRUCTURE-ACTIVITY RELATIONSHIP; XENOPUS LAEVIS;

EID: 9344269392     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960219h     Document Type: Article

References (34)

1. Reiter, R. J. Pineal melatonin: Cell biology of its synthesis and its physiological interactions. Endocrinol. Rev. 1991, 12, 151-180.
2. Pierpaoi, W. The pineal gland: a circadian or seasonal aging clock. Aging 1991, 3, 99-101.
3. (a) Waldhauser, F.; Ehrhart; B.; Förster, E. Clinical aspects of the melatonin action: impact of development, aging, and puberty, involvement of melatonin in psychiatric disease and importance of neuroimmunoendocrine interactions. Experientia 1993, 49, 671-681.
4. (b) Blehar, M. C.; Lewy, A. J. Seasonal mood disorders: consensus and controversy. Psychopharmacol. Bull. 1990, 4, 465-482.
5. Maestroni, G. J. M. The immunoneuroendocrine role of melatonin. J. Pineal Res. 1993, 14, 1-10.
6. Poeggeler, B.; Reiter, R. J.; Tan, D.-X.; Chen, L.-D.; Manchester, L. C. Melatonin, hydroxy radical-mediated oxidative damage, and aging: a hypothesis. J. Pineal Res. 1993, 14, 151-158.
7. 125I]iodomelatonin. J. Neuroendocrinol. 1989, 1, 315-320.
8. Kennaway, D. J.; Rowe, S. A. Melatonin binding sites and their role in seasonal reproduction. J. Reprod. Fertil. Suppl. 1995, 49, 423-435.
9. Pontoire, C.; Bernard, M.; Silvain, C.; Collin, J. P.; Voisin, P. Characterisation of melatonin binding sites in chicken and human intestines. Eur. J. Pharmacol. 1993, 247, 111-118.
10. (a) 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.
11. (b) 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.
12. 1b melatonin receptor. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 8734-8738.
13. (d) 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 chick brain. Neuron 1995, 15, 1003-1015.
14. (e) 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.
15. 125I]iodomelatonin-binding sites in the pigeon brain: binding characteristics, regional distribution and diurnal variation. J. Endocrinol. 1991, 128, 475-482.
16. (a) Steinhilber, D.; Brungs, M.; Werz, O.; Wiensenberg, I.; Danielsson, C.; Kahlen, J.-P.; Nayeri, S.; Schräder, M.; Carlberg, C. The nuclear receptor for melatonin represses 5-lipoxygenase gene expression in human B lymphocytes. J. Biol. Chem. 1995, 270, 7037-7040.
17. (b) Carlberg, C.; Wiesenberg, I. The orphan receptor family RZR/ROR, melatonin and 5-lipoxygenase: an unexpected relationship. J. Pineal Res. 1995, 18, 171-178.
18. (a) Heward, C. B.; Hadley, M. E. Structure activity-relationships of melatonin and related indoleamines. Life Sci. 1975, 17, 1167-1178.
19. (b) 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.
20. (c) 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. BioMed. Chem. Lett. 1994, 4, 1555-1558.
21. (a) 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-phenyltryptamines. J. Med. Chem. 1995, 38, 1132-1139.
22. (b) 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. BioMed. Chem. Lett. 1994, 4, 1559-1564.
23. (a) Yous, S.; Andrieux, J.; Howell, H. E.; Morgan, P. J.; Renard, P.; Pfeiffer, B.; Lesieur, D.; Guardiola-Lemaitre, B. Novel naphthalenic ligands with high affinity for the melatonin receptor. J. Med. Chem. 1992, 35, 1484-1486.
24. (b) Depreux, P.; Lesieur, D.; Mansour, H. A.; Morgan, P.; Howell, F.; Renard, P.; Caignard, D.-H.; Pfeiffer, B.; Delagrange, P.; Guardiola, B.; Yous, S.; Demarque, A.; Adam, G.; Andrieux, J. Synthesis and structure-activity relationships of novel naphthalenic and bioisosteric related amidic derivatives as melatonin receptor ligands. J. Med. Chem. 1994, 37, 3231-3239.
25. 125I]iodomelatonin binding sites. J. Med. Chem. 1995, 38, 2050-2060.
26. Jansen, J. M.; Karlén, A.; Grol, C. J.; Hacksell, U. Conformational properties of melatonin and two conformationally restricted agonists: a molecular mechanic and NMR spectroscopy study. Drug Design and Discovery; Harwood Academic Publishers GmbH: New York, 1993; Vol. 10, pp 115-133.
27. 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.
28. Langlois, M.; Gaudy, F. A new synthesis of 8-hydroxy-2-di-n-propylamino-tetralin (8-OH-DPAT). Synth. Commun. 1992, 22, 1723-1734.
29. (a) Violland, R.; Gaige, R.; Pacheco, H. Determination à l'aide de la RMN de la configuration d'α-amino-alcools cyclaniques apparentés à l'adrénaline. Bull. Soc. Chim. 1967, 2105-2106.
30. (b) Violland, R.; Violland-Duperret, N.; Pacheco, H. Psychotropes potentiels. IV. Synthèse de nouveaux α-amino-alcools cyclaniques apparentés à l'éphédrine et à la mescaline. Détermination de leur configuration à l'aide de la RMN. Chim. Ther. 1969, 2, 95-102.
31. Varie, D. L. Preparation of 1-benzoyl-4(amino)-1,2,-2a,3,4,5,-hexahydrobenzo[cd]indoles from L-tryptophan. Tetrahedron Lett. 1990, 31, 7583-7586.
32. Quay, W. B.; Bagnara, J. T. Relative potencies of indolic and related compounds in the body-lightening reaction of larval xenopus. Arch. Int. Pharmacodyn. 1984, 150, 137-143.
33. Hogben, L.; Slome, D. The pigmentary effector sytem: VI. The dual character of endocrine co-ordinationin amphibian colour chang. Proc. R. Soc. (London), Ser. B 1931, 108, 10-53.
34. Murphy, R. A.; Kung, H. F.; Kung, M.-P.; Billing, J. Synthesis and characterization if iodobenzamide analogues: potential D-2 dopamine receptor imaging agents. J. Med. Chem. 1990, 33, 171-178.