Design and synthesis of new N1 and C3-substituted 4-fluoroindolic melatoninergics

Current Drug Discovery Technologies

Volumn 4, Issue 3, 2007, Pages 198-207

  Tsotinis, Andrew ^a   Eleutheriades, Andreas ^a   Davidson, Kathryn ^b   Sugden, David ^b  

^a UNIVERSITY OF ATHENS   (Greece)

^b KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

Melatoninergic activity; Substituted 4 fluoroindoles; Synthesis

Indexed keywords

INDOLE DERIVATIVE; LUZINDOLE; MELATONIN; MELATONIN RECEPTOR; RAMELTEON; TRYPTAMINE DERIVATIVE;

ARTICLE; BINDING AFFINITY; CELL STRAIN 3T3; DRUG BINDING; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; NONHUMAN; PRIORITY JOURNAL; XENOPUS LAEVIS;

ANIMALS; CHROMATOGRAPHY; DRUG DESIGN; HUMANS; INDENES; INDOLES; IODINE RADIOISOTOPES; MASS SPECTROMETRY; MELANOPHORES; MELATONIN; MICE; MOLECULAR STRUCTURE; NIH 3T3 CELLS; PROTEIN BINDING; RADIOLIGAND ASSAY; RECEPTOR, MELATONIN, MT1; RECEPTOR, MELATONIN, MT2; TRANSITION TEMPERATURE; TRYPTAMINES; XENOPUS LAEVIS;

EID: 35948944333     PISSN: 15701638     EISSN: None     Source Type: Journal    
DOI: 10.2174/157016307782109715     Document Type: Article

References (40)

1. Caniato R., Filippini R., Piovan A., Puricelli L., Borsarini A., Cappelletti E.: Melatonin in plants. Adv. Exp. Med. Biol. 527, 593, (2003).
2. Garfinkel D., Laudon M., Nof D., Zisapel N.: Improvement of sleep quality in elderly people by controlled-release melatonin. Lancet 346, 541, (1995).
3. Wurtman R.: Ramelteon: a novel treatment for the treatment of insomnia. Expert Rev. Neurother. 6, 957, (2006).
4. Matsubara E., Bryant-Thomas T., Pacheco-Quinto J., Henry T.L., Poeggeler B., Herbert D., Cruz-Sanchez F., Chyan Y.J., et al.: Melatonin increases survival and inhibits oxidative and amyloid pathology in a transgenic model of Alzheimer's disease. J. Neurochem. 85, 1101, (2003).
5. Blask D.E., Dauchy R.T., Sauer L.A.: Putting cancer to sleep at night: the neuroendocrine/circadian melatonin signal. Endocrine 27, 179-188, (2005).
6. Reiter R.J., Tan D.X., Pappolla M.A.: Melatonin relieves the neural oxidative burden that contributes to dementias. Ann. N.Y. Acad. Sci. 1035, 179, (2004).
7. Reiter R.J.: Pineal melatonin: Cell biology of its synthesis and of its physiological interactions. Endocr. Rev. 12, 151, (1991).
8. Shida C.S., Castrucci A.M.L., Lamy-Freund M.T.: High melatonin solubility in aqueous medium. J. Pineal Res. 16, 198, (1994).
9. Pieri C., Marra M., Moroni F., Recchioni R., Marcheselli F.: Melatonin: A peroxyl radical scavenger more effective than vitamin E. Life Sci. 55, PL271, (1994).
10. Livrea M.A., Tesoriere L., D'Arpa D., Morreale M.: Reaction of melatonin with lipoperoxyl radicals in phospholipid bilayers. Free Radic. Biol. Med. 23, 706, (1997).
11. Iakovou K., Varvaresou A., Kourounakis A.P., Stead K., Sugden D., Tsotinis A.: Design, synthesis and biological evaluation of novel β-substituted indol-3-yl ethylamido melatoninergic analogues. J. Pharm. Pharmacol. 54, 147, (2002).
12. 2 melatonin receptors in mammals. Endocrine 27, 101, (2005).
13. Bittman E.L., Weaver D.R.: The distribution of melatonin binding sites in neuroendocrine tissues of the ewe. Biol. Reprod. 43, 986, (1990).
14. Reppert S.M., Weaver D.R., Ebisawa T.: Cloning and characterization of a mammalian melatonin receptor that mediates reproductive and circadian responses. Neuron 13, 1177, (1994).
15. 1b melatonin receptor. Proc. Natl. Acad. Sci. USA 92, 8734, (1995).
16. 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 15, 1003, (1995).
17. Mailliet F., Ferry G., Vella F., Berger S., Coge F., Chomarat P., Mallet C., Guenin S.P., et al.: Characterization of the melatoninergic MT3 binding site on the NRH:quinone oxidoreductase 2 enzyme. Biochem. Pharmacol. 71, 74, (2005).
18. Tsotinis A., Vlachou M., Papahatjis D.P., Calogeropoulou T., Nikas S.P., Garratt P.J., Piccio V., Vonhoff S., et al.: 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. J. Med. Chem. 49, 3509, (2006) and references cited therein.
19. Zlotos D.P.: Recent advances in melatonin receptor ligands. Arch. Pharm. (Weinheim) 338, 229, (2005) and references cited therein.
20. 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. 36, 4069, (1993).
21. Davies D.J., Faust R., Garratt P.J., Marivingt-Mounir C., Davidson K., Teh M.-T., Sugden, D.: Binding affinity and biological activity of oxygen and sulfur isosteres at melatonin receptors as a function of their hydrogen bonding capability. Bioorg. Chem. 32, 1, (2004).
22. 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. 4, 1555, (1994).
23. 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 phenylalkyl amides. J. Med. Chem. 39, 1797, (1996).
24. Tsotinis A., Vlachou M., Papahatjis D.P., Nikas S.P., Sugden, D.: An efficient synthesis of simple β,β′-cyclobisalkylated melatoninergic phenylalkylamides. Lett. Org. Chem. 4, 92, (2007).
25. 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. 287, 239, (1995).
26. Faust R., Garratt P.J., Jones R., Yeh L.-K., Tsotinis A., Panoussopoulou M., Calogeropoulou T., Teh M.-T., 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. 43, 1050, (2000).
27. Leclerc V., Depreux P., Lesieur D., Caignard D.H., Renard P., Delagrange P., Guardiola-Lemaitre B., Morgan P.: Synthesis and biological activity of conformationally restricted tricyclic analogs of the hormone. Bioorg. Med. Chem. Lett. 6, 1071, (1996).
28. 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. 4, 1321, (1996).
29. 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. 4, 1333, (1996).
30. 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. 124, 10236, (2002).
31. Sugden D., Davidson K., Hough K.A., Teh M.-T.: Melatonin, melatonin receptors and melanophores: A moving story. Pigment Cell Res. 17, 454, (2004).
32. Tsotinis A., Gourgourinis J., Eleutheriades A., Davidson K., Sugden, D.: Design and synthesis of new N-OMe fluoro-indole melatoninergics. Med. Chem. 3, 561, (2007).
33. Edwards P.N.: In Organofluorine Chemistry: Principles and Commercial Applications; R.E. Banks, B.E. Smart, J.C. Tatlow, Eds.; Plenum Press: New York, pp. 502-509, (1994).
34. Mor M., Rivara S., Silva C., Bordi F., Plazzi P.V., Spadoni G., Diamantini G., Balsamini C., et al.: Melatonin receptor ligands: Synthesis of new melatonin derivatives and comprehensive comparative molecular field analysis (CoMFA) study. J. Med. Chem. 41, 3831, (1998).
35. Tarzia G., Diamantini G., Di Giacomo B., Spadoni G., Esposti D., Nonno R., Lucini V., Pannacci M., et al.: 1-(2-Alkanamidoethyl)-6-methoxyindole derivatives: a new class of potent indole melatonin analogues. J. Med. Chem. 40, 2003, (1997).
36. Sugden D.: Aggregation of pigment granules in single cultured Xenopus laevis melanophores by melatonin analogues. Br. J. Pharmacol. 104, 922, (1991).
37. Sugden D.: Effect of putative melatonin receptor antagonists on melatonin-induced pigment aggregation in isolated Xenopus laevis melanophores. Eur. J. Pharmacol. 213, 405, (1992).
38. Teh M.-T., Sugden D.: The putative melatonin receptor antagonist GR128107 is a partial agonist on Xenopus laevis melanophores. Br. J. Pharmacol. 126, 1237, (1999).
39. Davies D.J., Garratt P.J., Tocher D.A., Vonhoff S., Davies J., Teh M.-T., Sugden D.: Mapping the melatonin receptor. 5. Melatonin agonists and antagonists derived from tetrahydrocyclopent[b]indoles, tetrahydrocarbazoles and hexahydrocyclohept[b]indoles. J. Med. Chem. 41, 451, (1998).
40. Surrey A. R.: Name Reactions in Organic Chemistry, 2nd Ed, Academic Press: New York, (1961).