Synthesis of benzocycloalkane derivatives as new conformationally restricted ligands for melatonin receptors

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 23, 1998, Pages 3325-3330

  Kloubert, S ^a   Mathe Allainmat M ^a   Andrieux, J ^a   Sicsic, S ^a   Langlois, M ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANE DERIVATIVE; MELATONIN RECEPTOR;

ARTICLE; BRAIN; CHEMICAL REACTION; CHICKEN; DRUG CONFORMATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; LIGAND BINDING; NONHUMAN; RECEPTOR AFFINITY;

EID: 0032402449     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00601-5     Document Type: Article

References (27)

1. 1. Reiter R.J. , Endocrinol. Rev., 1991, 12, 151.
2. 2. Klein D.C., Roseboom P.H., Coon S.L., TEM, 1996, 7, 106.
3. 3. Arendt J., Deacon S, Chronobiol. Int., 1997, 14, 185.
4. 4. Arendt J., Deacon S. , English J., Hampton S., Morgan L. , J. Sleep Res., 1995, 4, 74.
5. 5. Wirz-Justice A., Amstrong S.M., J. Sleep Res., 1996, 5, 137.
6. 6. Blehar M.C., Lewy A.J. , Psychopharmacol. Bull, 1990, 4, 465.
7. 7. Reiter R.J., Endocrinol. Rev., 1980, 1, 109.
8. 8. Blask D.E., Wilson S.T., Zalatan F., Cancer Research, 1997, 57, 1909.
9. 9. Morgan P.J., Barrett P., Hazlerigg D., Milligan G., Lawson W., Maclean A., Davidson G., J. Neuroendocrinol., 1995, 7, 361.
10. 10. Reppert S.M., Weaver D.R., Godson C., TIPS, 1996, 17, 100.
11. 11. Mahle C.D., Takaki K.S., Watson A.J., In: Annual Reports in Medicinal Chemistry, Bristol J A., ed., Academic Press, London 1997, 32, 31.
12. 12. Mathé-Allainmat M., Andrieux J., Langlois M., Exp. Opin. Ther. Patents 1997, 7, 1447.
13. 13. Garratt P.J., Vonhoff S., Rowe S.J., Sugden, D., Bioorg Med. Chem. Lett.. 1994, 4, 1559.
14. 14. Spadoni G., Balsammi C., Diamantani G., Di Giacomon B., Tarzia G., Mor M., Plazzi P.V., Rivara S., Lucini V., Nonno R., Pannaci M., Fraschini F., Stankov B.M., J. Med. Chem., 1997, 40, 1990.
15. 15. Sicsic S., Serraz I., Andrieux J., Brémont B., Mathé-Allainmat M., Poncet A., Shen S., Langlois M., J. Med. Chem., 1996, 40, 739.
16. 16. Langlois M., Brémont B., Shen S., Poncet A., Andrieux J., Sicsic S., Serraz I., Mathé-Allainmat M., Renard P., Delagrange P., J. Med. Chem., 1995, 38, 2050.
17. 17. Garratt P.J., Travard S., Vonhoff S., Tsotinis A., Sudgen D., J. Med. Chem., 1996, 39, 1797.
18. 18. Fourmaintraux E., Depreux P., Lesieur D., Guardiola-Lemaître B., Bennejean C., Delagrange P., Howell H.E., Bioorg. Med. Chem., 1998, 6, 9.
19. 19. Davies D.J., Garratt P.J., Tocher D.A., Vonhoff S., Davies J., Teh M-T., Sugden D., J. Med. Chem., 1998, 41, 451.
20. 20. 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., J. Med. Chem., 1994, 37, 3231.
21. 21. Harusawa S., Yoneda R., Kurihara T., Hamada Y., Shioiri T., Tetrahedron Lett., 1984, 25, 427.
22. 22. Smith P.A.S., Berry W.L., J. Org. Chem., 1961, 26, 27.
23. 23. Kametani T., Kajiwara M., Fukumoto K., Tetrahedron, 1974, 30, 1053
24. 24. CHIRALSEP (76170, La Fresnaye, France). Enantiomeric separation was achieved using a semi-preparative chiral HPLC column CHIROSE BOND C1 (10μm-250×10mm) and a heptane/AcOEt/EtOH mobile phase.
25. 25. Takeda Chem. Ind. Ltd, WO9705098.
26. 26. Copinga S., Tepper P. G., Grol C. J., Horn A. S., Dubocovich M.L., J. Med. Chem., 1993, 36, 2891.
27. 27. Mathe-Allainmat M., Gaudy F., Sicsic S., Dangy-Caye A. L., Shen S., Bremont B, Benatalah Z., Langlois M., Renard P., Delagrange P., J. Med. Chem., 1996, 39, 3089.