1-(2-alkanamidoethyl)-6-methoxyindole derivatives: A new class of potent indole melatonin analogues

Journal of Medicinal Chemistry

Volumn 40, Issue 13, 1997, Pages 2003-2010

  Tarzia, Giorgio ^a   Diamantini, Giuseppe ^a   Di Giacomo, Barbara ^a   Spadoni, Gilberto ^a   Esposti, Daniele ^b   Nonno, Romolo ^c   Lucini, Valeria ^c   Pannacci, Marilou ^c   Fraschini, Franco ^c   Stankov, Bojidar Michaylov ^c  

^a UNIVERSITY OF URBINO   (Italy)

^b UNIVERSITY OF MILAN   (Italy)

^c UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIC AMP; MELATONIN DERIVATIVE; METHOXYINDOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG HALF LIFE; DRUG ISOLATION; DRUG STRUCTURE; HYPOTHESIS; IMMUNOMODULATION; LIGAND BINDING; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

ANIMALS; BINDING SITES; BINDING, COMPETITIVE; CHICKENS; CYCLIC AMP; DRUG DESIGN; FORSKOLIN; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); INDOLES; MELATONIN; MODELS, CHEMICAL; QUAIL; SUPERIOR COLLICULUS;

EID: 15444338704     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960653j     Document Type: Article

References (37)

1. Reiter, R. J. Pineal melatonin: Cell biology of its synthesis and of its physiological interactions. Endocr. Rev. 1991, 12, 151-180.
2. Hagan, R. M.; Oakley, N. R. Melatonin comes of age? Trends Pharmacol. Sci. 1995, 16, 81-83.
3. Armstrong, S. M. Melatonin and circadian control in mammals. Experientia 1989, 45, 932-938.
4. 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.
5. Cahill, G. M.; Besharse, J. C. Circadian rhythmicity in vertebrate retinas: regulation by a photoreceptor oscillator. Progress in Retinal Eye Research; Elsevier Science Ltd.: Great Britain, 1995; Vol. 14, pp 267-291.
6. (a) Reiter, R. J.; Melchiorri, D.; Sewerynek, E.; Poeggeler, B.; Barlow-Walden, L.; Chuang, J. I.; Ortiz, G. G.; Acuna-Castroviejo, D. A review of the evidence supporting melatonin's role as an antioxidant. J. Pineal. Res. 1995, 18, 1-11.
7. (b) Huether, G. Melatonin as an antiaging drug: between facts and fantasy. Gerontology 1996, 42, 87-96.
8. (c) Giusti, P.; Lipartiti, M.; Franceschini, D.; Schiavo, N.; Floreani, M.; Manev, H. Neuroprotection by melatonin from kainate-induced exitotoxicity in rats. FASEB J. 1996, 10, 891-895.
9. Maestroni, G. J. M. The immunoneuroendocrine role of melatonin. J. Pineal. Res. 1993, 14, 1-10.
10. (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.
11. (b) Dubocovic, M. L. Melatonin receptors: are there multiple subtypes? Trends Pharmacol. Sci. 1995, 16, 50-56.
12. Spadoni, G.; Balsamini, C.; Diamantini, G.; Di Giacomo, B.; Tarzia, G.; Mor, M.; Plazi, P. V.; Rivara, S.; Lucini, V.; Nonno, R.; Pannacci, M.; Fraschini, F.; Stankov, B. M. 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 N. W. S.; Lewis, D. F. V. Structural requirements at the melatonin receptor. Br. J. Pharmacol. 1995, 114, 618-623.
14. (a) Depreux, P.; Lesieur, D.; Mansour, H. A.; Morgan, P.; Howell, H. E.; 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 nafthalenic and bioisosteric related amidic derivatives as melatonin receptor ligands. J. Med. Chem. 1994, 37, 3231-3239.
15. 125I]Iodomelatonin binding sites. J. Med. Chem. 1995, 38, 2050-2060.
16. (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.
17. 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.
18. Taborsky, R. G.; Delvigs, P.; Page, I. H. 6-Hydroxyindoles and the metabolism of melatonin. J. Med. Chem. 1965, 8, 855-858.
19. Allen, M. S.; Hamaker, L. K.; La Loggia, A. J.; Cook, J. M. Entry into 6-methoxy-D(+)-tryptophans. Stereospecific synthesis of 1-benzensulfonyl-6-methoxy-D(+)-tryptophan ethyl ester. Synth. Commun. 1992, 22, 2077-2102.
20. Kline, T. Preparation of 2-Iodotryptamine and 2-Iodo-5-methoxytryptamine. J. Heterocycl. Chem. 1985, 22, 505-509.
21. Bergman, J.; Venemalm, L. Efficient synthesis of 2-chloro-, 2-bromo-, and 2-iodoindole. J. Org. Chem. 1992, 57, 2495-2497.
22. Houlihan, W. J.; Parrino, V. A.; Uike, Y. Lithiation of N-(2-alkylphenyl)alkanamides and related compounds. A modified Madelung indole synthesis. J. Org. Chem. 1981, 46, 4511-4515.
23. Kasahara, A.; Izumi, T.; Kikuchi, T.; Lin, X. Synthesis of indole derivatives from 2-bromoanilines by a palladium-assisted reaction. J. Heterocycl. Chem. 1987, 24, 1555-1556.
24. Gatta, F.; Chiavarelli, S. Pirazino(1,2-a)-E 1,4-diazepino(1,2-a)indoli. Il Farmaco Ed. Sc. 1975, 30, 631-641.
25. (a) 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.
26. (b) Ying, S. W.; Rusak, B.; Delagrange, P.; Mocaer, E.; Renard, P.; Guardiola-Lemaitre, B. Melatonin analogues as agonists and antagonists in the circadian system and other brain areas. Eur. J. Pharmacol. 1996, 296, 33-42.
27. Cozzi, B.; Stankov, B.; Viglietti-Panzica, C.; Capsoni, S.; Aste, N.; Lucini, V.; Fraschini, F.; Panzica, G. C. Distribution and characterization of melatonin receptor in the brain of the Japanese quail, Coturnix japonica. Neurosci. Lett. 1993, 150, 149-152.
28. 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.
29. 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.
30. Morgan, P. J.; Barret, P.; Howell, H. E.; Helliwell, R. Melatonin receptors: localization, molecular pharmacology and physiological significance. Neurochem. Int. 1994, 24, 101-146.
31. Birnbaumer, L.; Abramowitz, J.; Brown, A. M. Receptor-effector coupling by G-protein. Biochim. Biophys. Acta 1990, 1031, 163-224.
32. 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.
33. 2-dopamine receptor of the anterior pituitary gland. Mol. Pharmacol. 1984, 26, 214-227.
34. Costa, T.; Ogino, Y.; Munson, P. J.; Onaran, H. O.; Rodbard, D. Drug efficacy at guanine nucleotide binding regulatory protein linked receptors: Thermodinamic interpretation of negative antagonism and of receptor activity in the absence of ligand. Mol. Pharmacol. 1992, 41, 549-560.
35. 2-adrenoceptors. Arch. Pharmacol. 1982, 321, 253-259.
36. Duranti, E.; Stankov, B.; Spadoni, G.; Duranti, A.; Lucini, V.; Capsoni, S.; Biella, G.; Fraschini, F. 2-Bromomelatonin: Synthesis and characterization of a potent melatonin agonist. Life Sci. 1992, 51, 479-485.
37. 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.