Stereoselective synthesis of 4-amino-3-hydroxy-4,5,6,6a-tetrahydro-3aH- cyclopenta[d]isoxazole-4-carboxylic acid, a conformationally constrained analogue of aspartic acid

Synthesis

Volumn , Issue 14, 2007, Pages 2145-2148

  Conti, Paola ^a   Pinto, Andrea ^a   Roda, Gabriella ^a   Tamborini, Lucia ^a   Arosio, Dario ^a   De Micheli, Carlo ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

1,3 dipolar cycloaddition; Aspartate analogues; Glutamate transporters; Heterocycles; Stereoselective synthesis

Indexed keywords

ASPARTATE ANALOGUES; DIPOLAR CYCLOADDITION; GLUTAMATE TRANSPORTERS; HETEROCYCLES; STEREOSELECTIVE SYNTHESIS;

CATALYTIC OXIDATION; CYCLOADDITION; DERIVATIVES; REGIOSELECTIVITY; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

CARBOXYLIC ACIDS;

4 AMINO 3 HYDROXY 4,5,6,6A TETRAHYDRO 3AH CYCLOPENTA[D]ISOXAZOLE 4 CARBOXYLIC ACID; AMINE; AMINO ACID; ASPARTIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; CYANIDE; IMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFORMATION; CYCLOADDITION; MICROWAVE IRRADIATION; OXIDATION; POLYMERIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 34547217373     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983750     Document Type: Article

References (19)

1. (a) Fonnum, F. J. Neurochem. 1984, 42, 1.
2. (b) Collingridge, G. L.; Lester, R. A. J. Pharmacol. Rev. 1989, 40, 143.
3. (c) Headley, P. M.; Grillner, S. Trends Pharmacol. Sci. 1990, 11, 205.
4. (a) Olney, J. W. Science 1969, 164, 719.
5. (b) Olney, J. W. Annu. Rev. Pharmacol. Toxicol. 1990, 30, 47.
6. (c) Choi, D. W.; Rothman, S. M. Annu. Rev. Neurosci. 1990, 13, 171.
7. Johnston, G. A. R. In Glutamate: Transmitter in the Central Nervous System; Roberts, P. J.; Storm-Mathisen, J.; Johnston, G. A. R., Eds.; Wiley: Chichester, 1981, 77-87.
8. (a) Barbour, B.; Brew, H.; Attwell, D. Nature 1988, 335, 433.
9. (b) Szatkowski, M.; Barbour, B.; Attwell, D. Brain Res. 1991, 555, 343.
10. Sims, K. D.; Robinson, M. B. Crit. Rev. Neurobiol. 1999, 13, 169.
11. Danbolt, N. C. Prog. Neurobiol. 2001, 65, 1.
12. Levi, G.; Raiteri, M. Trends Neurosci. 1993, 16, 415.
13. (a) Fletcher, E. J.; Johnston, G. A. R. J. Neurochem. 1991, 57, 911.
14. (b) Robinson, M. B.; Sinor, J. D.; Dowd, L. A.; Kerwin, J. F. J. J. Neurochem. 1993, 60, 167.
15. Conti, P.; De Amici, M.; De Sarro, G.; Rizzo, M.; Stensbal, T. B.; Bräuner-Osborne, H.; Madsen, U.; Toma, L.; De Micheli, C. J. Med. Chem. 1999, 42, 4099.
16. Funicello, M.; Conti, P.; De Amici, M.; De Micheli, C.; Mennini, T.; Gobbi, M. Mol. Pharmacol. 2004, 66, 522.
17. Conti, P.; De Amici, M.; Grazioso, G.; Roda, G.; Stensbøl, T. B.; Bräuner-Osborne, H.; Madsen, U.; Toma, L.; De Micheli, C. Eur. J. Org. Chem. 2003, 4455.
18. Conti, P.; Roda, G.; Stabile, H.; Vanoni, M. A.; Curti, B.; De Amici, M. Farmaco 2003, 58, 683.
19. Vyas, D. M.; Chiang, Y.; Doyle, T. W. Tetrahedron Lett. 1984, 25, 487.