First enantiospecific synthesis of a 3,4-dihydroxy-L-glutamic acid [(3S,4S)-DHGA], a new mGluR1 agonist

Bioorganic and Medicinal Chemistry Letters

Volumn 10, Issue 2, 2000, Pages 129-133

  Dauban, Philippe ^a   De Saint Fuscien, Carole ^a   Acher, Francine ^b   Prézeau, Laurent ^c   Brabet, Isabelle ^c   Pin, Jean Philippe ^c   Dodd, Robert H ^a  

^a CNRS   (France)

^b UNIVERSITÉ PARIS DESCARTES   (France)

^c CNRS UPR 9023   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL ALCOHOL; CARBOXYLIC ACID DERIVATIVE; GLUTAMIC ACID DERIVATIVE; METABOTROPIC RECEPTOR; RIBOSE;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; CONFORMATIONAL TRANSITION; NONHUMAN; STEREOISOMERISM; SYNTHESIS;

EID: 0034677089     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00641-1     Document Type: Article

References (39)

1. Krogsgaard-Larsen P., Ebert B., Lund T.M., Bräuner-Osborne H., Slok F.A., Johansen T.N., Brehm L., Madsen U. Eur. J. Med. Chem. 31:1996;515.
2. Knöpfel T., Kuhn R., Allgeier H. J. Med. Chem. 38:1995;1417.
3. Nakanishi S. Science. 258:1992;597.
4. Conn P., Pin J.-P. Ann. Rev. Pharmacol. Toxicol. 37:1997;205.
5. Madge, D. J.; Batchelor, A. M. Ann. Rep. Med. Chem.; Academic Press, 1996; Chapter 4.
6. Shimamoto K., Ishida M., Shinozaki H., Ohfune Y. J. Org. Chem. 56:1991;4167.
7. Yanagida M., Hashimoto K., Ishida M., Shinozaki H., Shirahama H. Tetrahedron Lett. 30:1989;3799.
8. Gu Z.Q., Hesson D.P., Pelletier J.C., Maccechini M.L., Zhou L.M., Skolnick P. J. Med. Chem. 38:1995;2518.
9. Ezquerra J., Pedregal C., Mico I., Najera C. Tetrahedron: Asymmetry. 5:1994;921.
10. Moody C.M., Young D.W. Tetrahedron Lett. 35:1994;7277.
11. Kozikowski A.P., Steensma D., Araldi G.L., Tückmantel W., Wang S., Pshenichkin S., Surina E., Wroblewski J.T. J. Med. Chem. 41:1998;1641.
12. Ouerfelli, O.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Synlett 1993, 409.
13. Ornstein P.L., Bleisch T.J., Arnold M.B., Wright R.A., Johnson B.G., Schoepp D.D. J. Med. Chem. 41:1998;346.
14. Wermuth C.G., Mann A., Schoenfelder A., Wright R.A., Johnson B.G., Burnett J.P., Mayne N.G., Schoepp D.D. J. Med. Chem. 39:1996;814.
15. Escribano A., Ezquerra J., Pedregal C., Rubio A., Yruretagoyena B., Baker S.R., Wright R.A., Johnson B.G., Schoepp D.D. Bioorg. Med. Chem. Lett. 8:1998;765.
16. Helaine V., Bolte J. Tetrahedron: Asymmetry. 9:1998;3855.
17. Pin J.-P., De Colle C., Bessis A.-S., Acher F. Eur. J. Pharmacol. 375:1999;277.
18. Todeschi N., Gharbi-Benarous J., Acher F., Larue V., Pin J.-P., Bockaert J., Azerad R., Girault J.-P. Bioorg. Med. Chem. 5:1997;335.
19. Braüner-Osborne H., Nielsen B., Stensbøl T.B., Johansen T.N., Skjaerbaek N., Krogsgaard-Larsen P. Eur. J. Pharmacol. 335:1997;R1.
20. Jullian N., Brabet I., Pin J.-P., Acher F. J. Med. Chem. 42:1999;1546.
21. Virtanen A.I., Ettala T. Suomen Kemistilehti. B29:1956;107.
22. Virtanen A.I., Ettala T. Acta Chem. Scand. 11:1957;182.
23. Muller A.L., Uusheimo K. Acta Chem. Scand. 19:1965;1987.
24. Dubois, L.; Dodd, R. H. Tetrahedron 1993, 49, 901.
25. Dubois L., Mehta A., Tourette E., Dodd R.H. J. Org. Chem. 59:1994;434.
26. Dauban P., Dubois L., Tran Huu Dau E., Dodd R.H. J. Org. Chem. 60:1995;2035.
27. Dauban P., Chiaroni A., Riche C., Dodd R.H. J. Org. Chem. 61:1996;2488.
28. Dauban P., Hofmann B., Dodd R.H. Tetrahedron. 53:1997;10743.
29. Dauban P., Dodd R.H. J. Org. Chem. 62:1997;4277.
30. Neises B., Steglich W. Angew. Chem., Int. Ed. Engl. 17:1978;522.
31. Full details of the experimental procedures and characterization of the products have been published elsewhere: Dauban, P.; De Saint-Fuscien, C.; Dodd, R. H. Tetrahedron 1999, 55, 7589.
32. +.
33. Gomeza J., Mary S., Brabet I., Parmentier M.-L., Restituito S., Bockaert J., Pin J.-P. Mol. Pharmacol. 50:1996;923.
34. Joly C., Gomeza J., Brabet I., Curry K., Bockaert J., Pin J.-P. J. Neurosci. 15:1995;3970.
35. As indicated in the introduction, mGluR2 and mGluR4 are negatively coupled to adenylyl cyclase. Because this transduction cascade is more difficult to measure in transient transfection assays than the stimulation of IP formation, the coupling of these receptors to phospholipase C was made possible by co-expressing them with a chimeric G-protein alpha subunit, Gqi9 (ref 36).
36. Watkins J.C., Collingridge G. Trends Pharmacol. Sci. 15:1994;333.
37. Bessis, A.-S.; Jullian, N.; Coudert, E.; Pin, J.-P.; Acher, F. Neuropharmacology 1999, in press.
38. The various conformations of L-glutamic acid are described as follows:
39. Structures of the selective agonists of the three mGluR groups depicted in Figure 2.