M. L. Gelmi et al. / Bioorg. Med. Chem. 15 (2007) 7581–7589
7589
2
5
2 ꢁC for 1 h. The incubation was halted while adding
mL of cold assay buffer. The content of the tubes
3119–3129; (e) Ma, D.; Ma, J.; Dai, L. Tetrahedron:
Asymmetry 1997, 8, 825–827; (f) Kozikowski, A. P.;
Steensma, D.; Araldi, G. L.; Tuckmantel, W.; Wang, S.;
Pshenichkin, S.; Surina, E.; Wroblewski, J. T. J. Med.
Chem. 1998, 41, 1641–1650; (g) Pellicciari, R.; Marinozzi,
M.; Costantino, G.; Natalini, B.; Moroni, F.; Pellegrini,
D. J. Med. Chem. 1999, 42, 2716–2720; (h) Bradley, D. M.;
Mapitse, R.; Thomson, N. M.; Hayes, C. J. J. Org. Chem.
was immediately filtered under vacuum through glass fi-
bre filters GF/C and washed three times with 5 mL of as-
say buffer using Brandel cell harvester. Filters were then
placed in vials with 4 mL of scintillation cocktail, and
radioactivity was measured by means of a beta-counter
(
Packard LS 1600).
2
002, 67, 7613–7617; (i) Battistini, L.; Curti, C.; Zanardi,
F.; Rassu, G.; Auzzas, L.; Casiraghi, G. J. Org. Chem.
004, 69, 2611–2613; (j) Baudy, R. B.; Sze, J. Y.; Butera, J.
2
Acknowledgments
A. Synth. Commun. 2004, 34, 3949–3954; (k) Ung, A. T.;
Pyne, S. G.; Batenburg-Nguyen, U.; Davis, A. S.; Sherif,
A.; Bischoff, F.; Lesage, A. S. J. Tetrahedron 2005, 61,
We thank Cariplo Foundation for financial support and
Psychoactive Drug Screening Program (Case Western
Reserve University, Cleveland, USA) for performing
screening on mGlu receptors.
1
803–1812.
7
8
. (a) Palmer, E.; Monaghan, D. T.; Cotman, C. W. Eur. J.
Pharmacol. 1989, 166, 585–587; (b) Joly, C.; Gomeza, J.;
Brabet, I.; Curry, K.; Bockaert, J.; Pin, J.-P. J. Neurosci.
1995, 15, 3970–3981.
. Acher, F. C.; Tellier, F. J.; Azerad, R.; Brabet, I. N.;
Fagni, L.; Pin, J. P. R. J. Med. Chem. 1997, 40, 3119–
Supplementary data
3129.
9. Kawashima, N.; Karasawa, J.; Shimazaki, T.; Chaki, S.;
Okuyama, S.; Yasuhara, A.; Nakazato, A. Neurosci. Lett.
Spectroscopic and analytical data for compounds exo-3,
0
0
1
endo-4, exo-7/7 , endo8/8 , (ꢀ)-1 and (ꢀ)-9. H NMR
spectra of 1 and of mixture 2,9. Supplementary data
2
005, 378, 131–134.
0. (a) Aghajanian, G. K.; Marek, G. J. Neuropharmacology
997, 36, 589–599; (b) Marek, G. J.; Wright, R. A.;
1
1
Schoepp, D. D.; Monn, J. A.; Aghajanian, G. K. J.
Pharmacol. Exp. Ther. 2000, 292, 76–87.
1
1. Martin-Ruiz, R.; Puig, M. V.; Celada, P.; Shapiro, D. A.;
Roth, B. L.; Mengod, G.; Artigas, F. J. Neurosci. 2001, 21,
References and notes
9
856–9866.
1
2
. (a) Danysz, W.; Parsons, C. G.; Bresink, I.; Quack, G.
Drug News Perspect. 1995, 8, 261–277; (b) Meldrum, B. S.
J. Nutr. 2000, 130, 1007S–1015S.
12. Wieronska, J. M.; Smialowska, M.; Branski, P.; Gaspa-
rini, F.; Klodzinska, A.; Szewczyk, B.; Palucha, A.;
Chojnacka-Wojcik, E.; Pilc, A. Neuropsychopharmacology
2004, 29, 514–521.
13. Stachowicz, K.; Chojnacka-Wojcik, E.; Klak, K.; Pilc, A.
Neuropharmacology 2007, 52, 306–312.
14. Caputo, F.; Clerici, F.; Gelmi, M. L.; Pellegrino, S.; Pilati,
T. Tetrahedron: Asymmetry 2006, 17, 61–67.
15. Abbiati, G.; Clerici, F.; Gambini, A.; Gelmi, M. L.; Pilati,
T. J. Org. Chem. 2001, 65, 6299–6304.
. (a) Conn, P. J.; Pin, J. P. Annu. Rev. Pharmacol. Toxicol.
1
997, 37, 205–237; (b) Schoepp, D. D.; Jane, D. E.; Monn,
L. A. Neuropharmacology 1999, 38, 1431–1476.
. Schoepp, D. D. J. Pharmacol. Exp. Ther. 2001, 299, 12–20.
. Thomas, N. K.; Woolley, M. L.; Miller, J. C.; Clark, B. P.;
Harris, J. R.; Jane, D. E.; Watkins, J. C. Soc. Neurosci.
Abstr. 1998, 28, 229.15.
3
4
5
. (a) Ornstein, P. L.; Schoepp, D. D.; Monn, J. A. Curr.
Pharm. Des. 1995, 1, 355–362; (b) Jullian, N.; Brabet, I.;
Pin, J.-P.; Acher, F. C. J. Med. Chem. 1999, 42, 1546–
1555; (c) Bertrand, H.-O.; Bessis, A.-S.; Pin, J.-P.; Acher,
F. C. J. Med. Chem. 2002, 45, 3171–3183.
16. Tager, H. S.; Christensen, H. N. J. Am. Chem. Soc. 1972,
94, 968–972.
17. Bueno, M. P.; Cativiela, C.; Finol, C.; Mayoral, J. A. Can.
J. Chem. 1987, 65, 2182–2186.
18. Cativiela, C.; Loper, P.; Mayoral, J. A. Tetrahedron:
Asymmetry 1991, 2, 449–456.
19. Cativiela, C.; Loper, P.; Mayoral, J. A. Tetrahedron:
Asymmetry 1990, 1, 379–388.
20. Lowry, O. H.; Rosenbrough, N. J.; Farr, A. L.; Randall,
R. J. J. Biol. Chem. 1951, 193, 265–266.
21. Dalpiaz, A.; Borea, P. A.; Gessi, S.; Gilli, S. Eur. J.
Pharmacol. 1996, 312, 107–114.
6
. (a) Curry, K.; Peet, M. J.; Magnuson, D. S. K.; McLen-
nan, H. J. Med. Chem. 1988, 31, 864–867; (b) Ezquerra, J.;
Yruretagoyena, B.; Avendano, C.; de la Cuesta, E.;
Gonzales, R.; Prieto, L.; Pedregal, C.; Espada, M.;
Prowse, W. Tetrahedron 1995, 51, 3271–3278; (c) Tellier,
F. J.; Acher, F. C.; Brabet, I. N.; Pin, J.-P.; Bockaert, J.;
Azerad, R. Bioorg. Med. Chem. Lett. 1995, 5, 2627–2632;
(d) Acher, F. C.; Tellier, F. J.; Azerad, R.; Brabet, I. N.;
Fagni, L.; Pin, J.-P. R. J. Med. Chem. 1997, 40,
22. Leysen, J. E.; Niemergeers, C. J.; Van Neuten, J. M.;
Laduron, P. M. Mol. Pharmacol. 1982, 21, 301–314.