Recent advances in melatonin receptor ligands

Archiv der Pharmazie

Volumn 338, Issue 5-6, 2005, Pages 229-247

  Zlotos, Darius P ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Melatonin receptors; MT1; MT2; Selective agonists; Selective antagonists

Indexed keywords

AGOMELATINE; ANTIDEPRESSANT AGENT; BENZOFURAN DERIVATIVE; BENZOXAZOLE DERIVATIVE; DIHYDRO 1,4 BENZODIOXIN DERIVATIVE; DIHYDROBENZOXATHIIN DERIVATIVE; G PROTEIN COUPLED RECEPTOR; INDAN DERIVATIVE; LIGAND; MELATONIN; MELATONIN 1; MELATONIN 1 RECEPTOR AGONIST; MELATONIN 1 RECEPTOR ANTAGONIST; MELATONIN 2; MELATONIN 2 RECEPTOR AGONIST; MELATONIN 2 RECEPTOR ANTAGONIST; MELATONIN DERIVATIVE; MELATONIN RECEPTOR; NAPHTHALENE DERIVATIVE; RAMELTEON; RECEPTOR SUBTYPE; TETRALIN DERIVATIVE; THIOCHROMAN DERIVATIVE; UNCLASSIFIED DRUG;

BINDING KINETICS; CIRCADIAN RHYTHM SLEEP DISORDER; DEPRESSION; DRUG CONFORMATION; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; HORMONE ACTION; HORMONE RECEPTOR INTERACTION; INSOMNIA; LIGAND BINDING; NONHUMAN; PRIORITY JOURNAL; REVIEW; STRUCTURE ACTIVITY RELATION; XENOPUS;

ANIMALS; CHEMISTRY, PHARMACEUTICAL; HUMANS; LIGANDS; MOLECULAR STRUCTURE; RECEPTOR, MELATONIN, MT1; RECEPTOR, MELATONIN, MT2;

EID: 21844433213     PISSN: 03656233     EISSN: None     Source Type: Journal    
DOI: 10.1002/ardp.200400996     Document Type: Review

References (114)

1. R. J. Reiter, Endocr. Rev. 1991, 12, 151-180.
2. N. S. Foulkes, J. Borjigin, S. H. Snyder, P. Sassone-Corsi, Trends Neurosci. 1997, 20, 487-492.
3. V. M. Cassone, Chronobiol Int. 1998, 15, 457-473.
4. D. N. Krause, G. G. Geary, S. Doolen, S. P. Duckies, Adv. Exp. Med. Biol. 1999, 460, 299-310.
5. R. J. Reiter, Ann Med. 1998, 30, 103-108.
6. M. P. Jones, M. A. Melan, P. A. Witt-Enderby, Cancer Lett. 2000, 151, 133-143.
7. M L. Dubocovich, J. Pharmacol. Exp. Ther. 1985, 234, 395-401.
8. P-K. Li, P A. Witt-Enderby, Drug Future 2000, 25, 945-957.
9. M. L. Dubocovich, J. S. Takahashi, Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 3916-3920.
10. M. L. Dubocovich, FASEB J. 1988, 2, 2765-2773.
11. M. L. Dubocovich, Trends Pharmacol. Sci. 1995, 16, 50-56.
12. M. L. Dubocovich, D. P Cardinali, P. Delagrange, D. N. Krause, A. D. Strosberg, D. Sugden, F. D. Yocca, "The IUPHAR Compendium of Receptor Characterization and Classification", IUPHAR Media, London, 2000, pp. 271-277.
13. S. M. Reppert, D. R. Weaver, T. Ebisawa, Neuron 1994, 13, 1177-1185.
14. S. M. Reppert, C. Godson, C. D. Mahle, D. R. Weaver, S. A. Slaugenhaupt, J. F. Gusella, Proc. Natl. Acad. Sci. 1995, 92, 8734-8738.
15. C. Liu, D. R. Weaver, X. Jin, L. P. Shearmon, R. L. Pieschl, V. K. Gribkoff, S. M. Reppert, Neuron 1997, 19, 91-102.
16. S. Doolen, D. N. Krause, M. L. Dubocovich, S. P. Duckles, Eur. J. Pharmacol. 1998, 345, 67-69.
17. K. N. Ting, N. A. Blaylock, D. Sugdeon, P. Delagrange, E. Scalbert, V. G. Wilson, Br. J. Pharmacol. 1999, 127, 987-995.
18. M. L. Dubocovich, K. Yun, W. M. Al-Ghoul, S. Benloucif, M. I., Masana, FASEB J. 1998, 12, 1211-1220.
19. M. L. Dubocovich, M. I., Masana, S. Iacob, D. M. Sauri, Naunyn Schmied Arch. Pharmacol. 1997, 355, 365-375.
20. T. Ebisawa, S. Karne, M. R. Lerner, S. M. Reppert, Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 6133-6137.
21. F. Liu, H. Yuan, K. S. Sugamori, FEBS Lett., 1995, 374, 273-278.
22. O. Nosjean, M. Ferro, F. Cogé, P. Beauverger, J.-M. Henlin, F. Lefoulon, J.-L. Fauchére, P. Delagrange, E. Canet, J. A. Boutin. J. Biol. Chem. 2000, 275, 31311-31317.
23. D. Steihilber, C. Carlberg, Exp. Opin. Ther. Patents 1999, 9, 281-290.
24. A. Oldani, L. Ferini-Strambi, M. Zucconi, B. Stankov, F. Fraschini, S. Smirne, Neuro Report 1994, 6, 132-134.
25. T. Nickeisen, A. Lang, L. Bergau, Adv. Pineal Res., 1991, 5, 303-306.
26. R. L. Sack, M. L. Blood, A. J. Lewy, Sleep, 1992, 15, 434-441.
27. N. E. Rosenthal, D. A. Sack, F. M. Jacobsen, S. P. James, B. L. Parry, J. Arendt, L. Tamarkin, T. A. Wehr, J. Neural. Transm. Suppl. 1986, 21, 257-267.
28. R. J. Reiter, Exp. Gerontol. 1995, 30, 199-212.
29. I. V. Zhdanova, R. J. Wurtman, H. J. Lynch, J. R. Ives, A. B. Dollins, C. Morabito, J. K. Matheson, D. L. Schomer, Clin. Pharmacol. Ther. 1995, 57, 552-558.
30. P. M. Liebmann, A. Wölfler, P. Felsner, D. Hofer, K. Schauenstein, Int. Arch. Allergy Immunol. 1997, 112, 203-211.
31. S. M. Hill, D. E. Blask, Cancer Res. 1988, 48, 6121-6126.
32. H. Pickering, S. Sword, S. Vonhoff, R. Jones, D. Sugden, Br. J. Pharmacol. 1996, 119, 379-387.
33. P. A. Witt-Enderby, P-K. Li, Vitam. Horm. 2000, 58, 321-354.
34. P-K. Li, P. A. Witt-Enderby, Drug Future 2000, 25, 945-957.
35. M. L. Dubocovich, Emerging Drugs 1999, 153-173.
36. M. Mathé-Allainmat, J. Andrieux, M. Langlois, Exp. Opin. Ther. Patents 1997, 7, 1447-1458.
37. C. D. Mahle, K. S. Takaki, A. J. Watson, Ann. Rep. Med. Chem. 1997, 32, 31-40.
38. M. Mor, P. P. Vincenzo, G. Spadoni, T. Giorgio, Curr. Med. Chem. 1999, 6, 501-518.
39. C. J. Groll, J. M. Jansen, Bioorg. Med. Chem. 1996, 4, 1333-1339.
40. N. W. Chong, J. E. Evans, D. Sugden, Biochem. Biophys. Res. Commun. 1993, 193, 1355-1361.
41. D. Sugden, N. W. Chong, D. F. Lewis, Br. J. Pharmacol. 1995, 114, 618-623.
42. S. Sicsic., I. Serraz, J. Andrieux, J. Med. Chem. 1997, 40, 739-748.
43. M. Mor, S. Rivara, C. Silva, J. Med. Chem. 1998, 41, 3831-3844.
44. G. Spadoni, B. Stankov, A. Duranti, J. Med. Chem. 1993, 36, 4069-4074.
45. S. Yous, J. Andrieux, H. E. Howell, P. J. Morgan, P. Renard, B. Pfeiffer, D. Lesieur, B. Guardiola-Lemaitre, J. Med. Chem. 1992, 35, 1484-1486.
46. Drug Future, 2003, 28, 7-13.
47. P. K. Li, G. H. Chu, M. L. Gillen, T. Parekh, P. A. Witt-Enderby, Bioorg. Med. Chem. Lett. 1997, 7, 2177-2180.
48. V. Leclerc, P. Depreux, D. Lesieur, D.H. Caignard, P. Renard, P. Delagrange, B. Guardiola-Lemaitre, P. Morgan, Bioorg. Med. Chem Lett. 1996, 6, 1071-1076.
49. P. Depreux, D. Lesieur, H. A. Mansour, P. Morgan, H. E. Howell, P. Renard, D.-H. Caignard, B. Pfeiffer, P. Delagrange, B. Guardiola, S. Vous, A. Demarque, G. Adam, J. Andrieux, J. Med. Chem. 1994 37, 3231-3239.
50. C. Marot, P. Chavatte, L. Morin-Allory, M.-C. Viaud, G. Guillaumet, P. Renard, D. Lesieur, A. Michel, J. Med. Chem. 1998 41, 4453-4465.
51. P. J. Garratt, S. Travard, S. Vonhoff, A. Tsotinis, D. Sugden, J. Med. Chem. 1996 39, 1797-1805.
52. J. M. Jansen, S. Copinga, G. Gruppen, E. J. Molinari, M. L. Dubocovich, C. J. Grol, Bioorg. Med. Chem. 1996, 4, 1321-1332.
53. D. Sugden, Eur. J. Pharmacol. 1994, 254, 271-275.
54. P. J. Garratt, S. Vonhoff, S. J. Rowe, D. Sugden, Bioorg. Med. Chem Lett. 1994, 4, 1559-1564.
55. D. Sugden, D. J. Davies, P. J. Garratt, R. Jones, S. Vonhoff, Eur. J. Pharmacol. 1995, 287, 239-243.
56. G. Spadoni, C. Balsamini, G. Diamantini, B. Di Giacomo, G. Tarzia, M. Mor, P. V. Plazzi, S. Rivara, V. Lucini, R. Nonno, M. Pannaci, F. Fraschini, B. M. Stankov, J. Med. Chem. 1997, 40, 1990-2002.
57. M. Maithe-Allainmat, F. Gaudy, S. Sicsic, A.-L. Dangy-Caye, S. Shen, B. Bremont, Z. Benatalah, M. Langlois, P. Renard, P. Delagrange, J. Med. Chem. 1996, 39, 3089-3095.
58. C. Jellimann, M. Mathé-Allainmat, J. Andrieux, P. Renard, P. Delagrange, M. Langlois, J. Med. Chem. 1999, 42, 1100-1105.
59. Glaxo Group Ltd., WO 95/29173 (1995)
60. Glaxo Group Ltd., WO 95/17405 (1995)
61. P. A. Witt-Enderby, M. L. Dubocovich, Mol. Pharmacol. 1996, 50, 166-174.
62. L. Brydon, L. Petit, P. de Coppet, P. Barret, P. J. Morgan, A. D. Strosberg, R. Jockers, Reprod. Nutr. Dev. 1999, 39, 315-324.
63. S. Conway, J. E. Drew, S. J. Canning, P. Barret, R. Jockers, A. D. Strosberg, B. Guardiola-Lemaitre, P. Delagrange, P. J. Morgan, FEBS Lett. 1997, 407, 121-126.
64. R. Nonno, V. Lucini, M. Pannaci, C. Mazzucchielli, D. Angeloni, F. Fraschini, B. M. Stankov, Br. J. Pharmacol. 1998, 124, 485-92.
65. J. Venecek, Physiol. Rev., 1998, 78, 687-721.
66. D. Sugden, L. K. Yeh, M. T. Teh, Reprod. Nutr. Dev. 1999, 39, 335-344.
67. P. A. Witt-Enderby, G. H. Chu, M. L. Gillen, P. K. Li, J. Med. Chem. 1997 40, 4195-4198.
68. C. B. Heward, M. E. Hadley, Life Sci. 1975, 17, 1167-1177.
69. M. L. Dubocovich, J. Pharmacol. Exp. Ther. 1988, 246, 902-910.
70. P. J. Garratt, R. Jones, D. A. Tocher, D. Sugden, J. Med. Chem. 1995 38, 1132-1139.
71. M. Masson-Pevet, J. Recio, H. Y. Guerrero, E. Mocaer, P. Delagrange, B. Guardiola-Lemaitre, P. Pevet, J. Pineal Res. 1998, 25, 172-176.
72. G. Tarzia, G. Diamantini, B. Di Giacomo, G. Spadoni, D. Esposti, R. Nonno, V. Lucini, M. Pannacci, F. Fraschini, B. M. Stankov, J. Med. Chem. 1997, 40, 2003-2010.
73. G. Spadoni, B. Stankov, A. Duranti, G. Biella, V. Lucini, A. Salvatori, F. Fraschini, J. Med. Chem. 1993, 36, 4069-4074.
74. G. Spadoni, C. Balsamini, A. Bedini, G. Diamantini, B. Di Giacomo, A. Tontini, G. Tarzia, M. Mor, P. V. Plazzi, S. Rivara, R. Nonno, M. Pannacini, V. Lucini, F. Fraschini, B. M. Stankov, J. Med. Chem. 1998, 41, 3624-3634.
75. R. Nonno, V. Lucini, G. Spadoni, M. Pannaci, A. Croce, D. Esposti, C. Balasamini, G. Tarzia, F. Fraschini, B. M. Stankov, J. Pineal Res. 2000, 29, 234-240.
76. A. Tsotinis, A. Eleutheriades, K. Hough, D. Sugden, Chem. Comm. 2003, 382-383.
77. M.-T. Teh, D. Sudgeon, Naunyn Schmied Arch. Pharmacol. 1998, 358, 522-528.
78. A. Tsotinis, M. Vlachou, A. Eleutheriades, E. Prinea, D. Ebreo, M.-T. Teh, D. Sugden, Chem. Pharm. Bull. 2002, 50, 31-39.
79. P. J. Garrett, R. Jones, D. A. Tocher, D. Sugden, J. Med. Chem. 1995, 38, 1132-1139.
80. A. Lira-Rocha, O. Espejo-Gonzáles, E. B. Naranjo-Rodriguez, Eur. J. Med. Chem. 2002, 37, 945-951.
81. Suven Life Sciences Ltd. India, WO2004048331
82. Suven Life Sciences Ltd. India, WO2004048328
83. A. Tsotinis, M. Panoussopoulou, S. Sivananthan, D. Sugden, Il Farmaco 2001, 56, 725-729.
84. A. Tsotinis, M. Panoussopoulou, K. Hough, D. Sugden, Eur. J. Pharm. Sci. 2003, 18, 297-304.
85. R. Faust, P. J. Garratt, R. Jones, L.-K. Yeh, A. Tsotinis, M. Panoussopoulou, T. Calogeropoulou, M.-T. Teh, D. Sugden, J. Med. Chem. 2000 43, 1050-1061.
86. M. J. Millan, A. Gobert, F. Lejeune, A. Dekeyne, J. Pharmacol. Exp. Therap. 2003, 306, 954-964.
87. E. Fourmaintraux, P. Depreux, D. Lesieur, B. Guardiola-Lemaitre, C. Bennejean, P. Delagrange, H. E. Howell, Bioorg. Med. Chem. 1998, 6, 9-13.
88. E. Belloli, C. Foulon, S. Yous, M.-P. Vaccher, J.-B. Bonte, C. Vaccher, J. Chromathogr. A 2001, 907, 101-113.
89. G. Gatti, G. Piersanti, G. Spadoni, Il Farmaco 2003, 58, 469-476.
90. S. Yous, S. Durieux-Poissonnier, E. Lipka-Belloli, H. Guelzim, C. Bochu, V. Audinot, J. A. Boutin, P. Delagrange, C. Bennejean, P. Renard, D. Lesieur, Bioorg. Med. Chem. 2003, 11, 753-759.
91. Laboratoires Servier, FR 2846963, 2004.
92. C. Pégurier, L. Morellato, E. Chahed, J. Andrieux, J.-P. Nicolas, J. A. Boutin, C. Bennejean, P. Delagrange, M. Langlois, M. Mathé- Allainmat, Bioorg. Med. Chem. 2003, 11, 789-800.
93. G.-H. Chu, P. A. Witt-Enderby, M. Jones, P.-K. Li, Chem. Pharm. Bull. 2002, 50, 272-275.
94. V. Audinot, F. Mailliet, C. Lahaye-Brasseur, A. Bonnaud, A. Le Gall, C. Amossé, S. Dromaint, M. Rodriguez, N. Nagel, J.-P. Galizzi, B. Malpaux, G. Guillaumet, D. Lesieur, F. Lefoulon, P. Renard, P. Delagrange, J.-A. Boulin, Naunyn Schmied Arch. Pharmacol. 2003, 367, 553-561.
95. C. Jellimann, M. Mathè-Allainmat, J. Andrieux, S. Kloubert, J. A. Boutin, J.-P. Nicolas, C. Bennejean, P. Delagrange, M. Langlois, J. Med. Chem, 2000, 43, 4051-4062.
96. O. Uchikava, K. Fukatsu, R. Tokunoh, M. Kawada, K. Matsumoto, Y. Imai, S. Hinuma, K. Kato, H. Nishikawa, K. Hirai, M. Miyamoto, S. Ohkawa, J. Med. Chem. 2002, 45, 4222-4239.
97. Drug Future, 2003, 28, 950-958.
98. K. Kato, K. Hirai, K. Nishiyama, O. Uchikawa, K. Fukatsu, S. Ohkawa, Y. Kawamata, S. Hinuma, M. Miyamoto, Neuropharmacology 2005, 48, 301-310.
99. C. Cajochen, Curr. Opin. Invest. Drugs 2005, 6, 114-121.
100. R. J. Mattson, J. D. Catt, D. Keavy, C. P. Sloan, J. Epperson, Q. Gao, D. B. Hodges, L. Iben, C. D. Mahle, E. R. Ryan, F. D. Yocca, Bioorg. Med. Chem. Lett. 2003, 13, 1199-1202.
101. J. R. Epperson, M. A. Bruce, J. D. Catt, J. A. Deskus, D. B. Hodges, G. N. Karageorge, D. J. Keavy, C. D. Mahle, R. J. Mattson, A. A. Ortiz, M. F. Parker, K. S. Takaki, B. T. Watson, J. P. Yevich, Bioorg. Med. Chem. 2004, 12, 4601-4611.
102. L.-Q. Sun, J. Chen, K. Takaki, G. Johnson, L. Iben, C. D. Mahle, E. Ryan, C. Xu, Bioorg. Med. Chem. Lett. 2004, 14, 1197-1200.
103. L.-Q. Sun, J. Chen, M. Bruce, J. A. Deskus, J. R. Epperson, K. Takaki, G. Johnson, L. Iben, C. D. Mahle, E. Ryan, C. Xu, Bioorg. Med. Chem. Lett. 2004, 14, 3799-3802.
104. L.-Q. Sun, K. Takaki, J. Chen, L. Iben, J. O. Knipe, L. Pajor, C. D. Mahle, E. Ryan, C. Xu Bioorg. Med. Chem. Lett. 2004, 14, 5157-5160.
105. J. R. Epperson, J. A. Deskus, A. J. Gentile, L. G. Iben, E. Ryan, N. S. Sarbin, Bioorg. Med. Chem. Lett. 2004, 14, 1023-1026.
106. N. N. Vachharajani, K: Yeleswaram, D. W. Boulton, J. Pharm. Sci., 2003, 4, 760-772.
107. I. Charton, A. Mamai, C. Bennejean, P. Renard, E. H. Howell, B. Guardiola-Lemaitre, P. Delagrange, P. J. Morgan, M.-C. Viaud, G. Guillaumet, Bioorg. Med. Chem. 2000, 8, 105-114.
108. V. Lucini, M. Pannacci, F. Scaglione, F. Fraschini, S. Rivara, M. Mor, F. Bordi, P. V. Plazzi, G. Spadoni, A. Bedini, G. Piersati, G. Diamantini, G. Tarzia, J. Med. Chem. 2004, 47, 4202-4212.
109. D. J. Davies, R. Faust, P. J. Garratt, C. Marivingt-Mounir, K. Davidson, M-T. Teh, D. Sugden, Bioorg. Chemistry 2004, 32, 1-12.
110. W. S. Messer Jr., Curr. Pharm. Design 2004, 10, 2015-2020.
111. C. Descamps-Francois, S. Yous, P. Chavatte, V. Audinot, A. Bonnaud, J. A. Boutin, P. Delagrange, C. Bennejean, P. Renard, D. Lesieur., J. Med. Chem. 2003, 46, 1127-1129.
112. M. A. Ayoub, C. Couturier, E. Lucas-Meunier, S. Angers, P. Fossier, M. Bouvier, R. Jockers, J. Biol. Chem. 2002, 277, 21522-21528.
113. C. Larraya, J. Guillard, P. Renard, V. Audinot, J. A. Boutin, P. Delagrange, C. Bennejean, M.-C. Viaud-Massuard, Eur. J. Med. Chem. 2004, 39, 515-526.
114. J. Guillard, C. Larraya, M.-C. Viaud-Massuard, Heterocycles 2003, 60, 865-877.