Synthesis of 3-hydroxy- and 3-carboxy-Δ2-isoxazoline amino acids and evaluation of their interaction with GABA receptors and transporters

European Journal of Organic Chemistry

Volumn , Issue 24, 2006, Pages 5533-5542

  Conti, Paola ^a   De Amici, Marco ^a   Pinto, Andrea ^a   Tamborini, Lucia ^a   Grazioso, Giovanni ^a   Frølund, Bente ^b   Nielsen, Birgitte ^b   Thomsen, Christian ^c   Ebert, Bjarke ^c   De Micheli, Carlo ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF COPENHAGEN   (Denmark)

^c H LUNDBECK A S   (Denmark)

Author keywords

2 Isoxazoline amino acids; Amino acids; Binding affinity; GABA receptors and transporters; Neurotransmitters

Indexed keywords

EID: 33845933524     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600628     Document Type: Article

References (26)

1. G. Sperk, S. Furtinger, C. Schwarzer, S. Pirker Advances in Experimental Medicine & Biology. 2004, 548, 92-103.
2. G. B. Richerson, Y. Wu, Advances in Experimental Medicine & Biology 2004, 548, 76-91.
3. R. B. Lydiard, J. Clin. Psychiatry 2003, 64, 21-27 (Suppl. 3).
4. I. W. Tremont-Lukats, C. Megeff, M. M. Backonja, Drugs 2000, 60, 1029-1052.
5. S. J. Enna, N. G. Bowery (Eds.), The GABA Receptors, The Humana Press: Totowa, NJ, 1997.
6. P. Krogsgaard-Larsen, B. Frolund, U. Kristiansen, K. Frydenvang, B. Ebert, Eur. J. Pharm. Sci. 1997, 5, 355-384.
7. M. Chebib, G. A. R. Johnston, J. Med. Chem. 2000, 43, 1427-1447.
8. P. Krogsgaard-Larsen, G. A. R. Johnston, D. R. Curtis, C. J. A. Game, R. M. McCulloch, J. Neurochem. 1975, 25, 803-809.
9. P. Krogsgaard-Larsen, G. A. R. Johnston, D. Lodge, D. R. Curtis, Nature 1977, 268, 53-55.
10. J. Faulhaber, A. Steiger, M. Lancel, Psychopharmacology (Berlin) 1997, 130, 285-291.
11. S. I. Stórustovu, B. Ebert, J. Pharmacol. Exp. Ther. 2006, 316, 1351-1359.
12. P. Krogsgaard-Larsen, G. A. R. Johnston, J. Neurochem. 1975, 25, 797-802.
13. E. Falk, J. Perregaard, B. Frølund, B. Søkilde, A. Buur, L. M. Hansen, K. Frydenvang, L. Brehm, T. Bolvig, O. M. Larsson, C. Sanchez, H. S. White, A. Schousboe, P. Krogsgaard-Larsen, J. Med. Chem. 1999, 42, 5402-5414.
14. R. Nordmann, P. Graff, R. Maurer, B. H. Gähwiler, J. Med. Chem. 1985, 28, 1109-1111.
15. P. Krogsgaard-Larsen, L. Nielsen, E. Falch, D. R. Curtis, J. Med. Chem. 1985, 28, 1612-1617.
16. D. M. Vyas, Y. Chiang, T. W. Doyle, Tetrahedron Lett. 1984, 25, 487-490.
17. A. P. Kozikowski, M. Adamcz, J. Org. Chem. 1983, 48, 366-372.
18. Y. Tsuzuki, K. Chiba, K. Mizuno, K. Tomita, K. Suzuki, Tetrahedron: Asymmetry 2001, 12, 2989-2997.
19. D. P. Curran, A. G. Scott, C. Sung-Mo, Heterocycles 1993, 35, 1371-1395.
20. P. Conti, M. De Amici, S. Joppolo di Ventimiglia, T. B. Stensbøl, U. Madsen, H. Bräuner-Osborne, E. Russo, G. De Sarro, G. Bruno, C. De Micheli, J. Med. Chem. 2003, 46, 3102-3108.
21. P. Caramella, G. Cellerino, Tetrahedron Lett. 1974, 2, 229-232.
22. B. Frølund, L. S. Jensen, L. Guandalini, C. Canillo, H. T. Vestergaard, U. Kristiansen, B. Nielsen, T. B. Stensbøl, U. Madsen, P. Krogsgaard-Larsen, T. Liljefors, J. Med. Chem. 2005, 48, 427-439.
23. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foreman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, GAUSSIAN 03, revision C.02, Gaussian, Inc., Wallingford, CT, 2004.
24. B. Frølund, L. Tagmose, T. Liljefors, T. Bryan Stensbøl, C. Engblom, U. Kristiansen, P. Krogsgaard-Larsen, J. Med. Chem. 2000, 43, 4930-4933.
25. Synthesis and ring-opening reactions of the diastereoisomeric cis- and trans-epoxides derived from 3-(benzyloxy)cyclopentene and 2-(benzyloxy)-2,5-dihydrofuran P. Crotti, V. Di Bussolo, L. Favero, F. Macchia, M. Pineschi, Eur. J. Org. Chem. 1998, 1675-1686.
26. V. Barone, M. Cossi, J. Phys. Chem. A 1998, 102, 1995-2001.