Rational design, synthesis, and pharmacological evaluation of 2-azanorbornane-3-exo,5-endo-dicarboxylic acid: A novel conformationally restricted glutamic acid analogue

Journal of Organic Chemistry

Volumn 68, Issue 4, 2003, Pages 1489-1495

  Bunch, Lennart ^a   Liljefors, Tommy ^a   Greenwood, Jeremy R ^a   Frydenvang, Karla ^a   Bräuner Osborne, Hans ^a   Krogsgaard Larsen, Povl ^a   Madsen, Ulf ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

GLUTAMIC ACID;

CATALYSTS; CONFORMATIONS; DRUG PRODUCTS; STOICHIOMETRY; SYNTHESIS (CHEMICAL);

CARBOXYLIC ACIDS;

2 AZANORBORNANE 3,5 DICARBOXYLIC ACID; ALPHA AMINO 3 HYDROXY 5 METHYL 4 ISOXAZOLEPROPIONIC ACID; BORNANE DERIVATIVE; GLUTAMATE RECEPTOR; GLUTAMATE RECEPTOR AGONIST; GLUTAMIC ACID DERIVATIVE; KAINIC ACID; RECEPTOR SUBTYPE; TRITIUM; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; DRUG RECEPTOR BINDING; NEUROTRANSMISSION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY DIFFRACTION;

ALPHA-AMINO-3-HYDROXY-5-METHYL-4-ISOXAZOLEPROPIONIC ACID; AZA COMPOUNDS; DICARBOXYLIC ACIDS; GLUTAMIC ACID; INHIBITORY CONCENTRATION 50; KAINIC ACID; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; MOLECULAR MIMICRY; MOLECULAR STRUCTURE; NORBORNANES; RECEPTORS, GLUTAMATE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037458793     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026509p     Document Type: Article

References (46)

1. For a recent review on the glutamate area, see: Bräuner-Osborne, H.; Egebjerg, J.; Nielsen, E.; Madsen, U.; Krogsgaard-Larsen, P. J. Med. Chem. 2000, 43, 2609-2645 and references therein.
2. Pellicciari, R.; Raimondo, M.; Marinozzi, M.; Natalini, B.; Costantino, G.; Thomsen, C. J. Med. Chem. 1996, 39, 2874-2876.
3. Pellicciari, R.; Marinozzi, M.; Camaioni, E.; Nùnez, M. del C.; Costantino, G.; Gasparini, F.; Giorgi, G.; Macchiarulo, A.; Subramanian, N. J. Org. Chem. 2002, 67, 5497-5507.
4. Kozikowski, A. P.; Steensma, D.; Araldi, G. L.; Tückmantel, W.; Wang, S. M.; Pshenichkin, S.; Surina, E.; Wroblewski, J. T. J. Med. Chem. 1998, 41, 1641-1650.
5. Tellier, F.; Acher, F.; Brabet, I.; Pin, J.-P.; Azerad, R. Bioorg. Med. Chem. 1998, 6, 195-208.
6. Hart, B. P.; Rapoport, H. J. Org. Chem. 1999, 64, 2050-2056.
7. (a) Armstrong, N.; Gouaux, E. Neuron 2000, 28, 165-181. Brookhaven PDB-file name for -Glu crystallized with iGluR2: 1FTJ.
8. (b) Brookhaven PDB-file name for kainate crystallized with iGluR2: 1FTO.
9. Nielsen, P.; Liljefors, T. J. Comput. Aided. Mol. Des. 2001, 15, 753-763.
10. Kunishima, N.; Shimada, Y.; Tsuji, Y.; Sato, T.; Yamamoto, M.; Kumasaka, T.; Nakanishi, S.; Jingami, H.; Morikawa, K. Nature 2000, 407, 971-977. Brookhaven PDB-file name for -Glu crystallized with mGluR1: 1EWK.
11. Energy minimization of 1 was carried out with MMFF94 for aqueous solution, using the Macromodel program (Schrödinger Inc.).
12. The commercial docking code Glide 1.8 (Glide 1.8, 2001; Schrödinger, Inc.: 1500 S. W. First Avenue, Suite 1180, Portland, OR 97201) was used with the recommended protein preparation steps and default settings.
13. Conti, P.; De Amici, M.; De Sarro, G.; Rizzo, M.; Stensbøl, T. B.; Bräiuner-Osborne, H.; Madsen, U.; Toma, L.; De Micheli, C. J. Med. Chem. 1999, 42, 4099-4107.
14. Jung, M. E.; Shishido, K.; Light, L.; Davis, L. Tetrahedron Lett. 1981, 22, 4607-4610.
15. Yamazaki, H.; Horikawa, H.; Nishitani, T.; Iwasaki, T.; Nosaka, K.; Tamaki, H. Chem. Pharm. Bull. 1992, 40, 102-108.
16. (a) Husbands, S. M.; Kline, R. H.; Allen, A. C.; Newman, A. H. J. Org. Chem. 1998, 63, 418-419.
17. (b) Campell, J. A.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616.
18. Bergmeier, S. C.; Cobas, A. A.; Rapoport, H. J. Org. Chem. 1993, 58, 2369-2376.
19. Bergmeier, S. C.; Stephen, C.; Lee, W. K.; Rapoport, H. J. Org. Chem. 1993, 58, 5019-5022.
20. Klaver, W. J.; Moolenaar, M. J.; Heimstra, H.; Speckamp, W. N. Tetrahedron 1988, 44, 3805-3818.
21. Boeckman, R. K.; Connell, B. T. J. Am. Chem. Soc. 1995, 117, 12368-12369.
22. Coldham, I.; Fernandez, J.-C.; Price, K. N.; Snowden, D. J. J. Org. Chem. 2000, 65, 3788-3795.
23. Calí, P.; Begtrup, M. Synthesis 2002, 63-66.
24. For examples of aza-Wittig reactions with aldehydes at room temperature, see: Palacios, F.; Alonso, C.; Rubiales, G. J. Org. Chem. 1997, 62, 1146-1154.
25. Malpass, J. R.; Cox, C. D. Tetrahedron Lett. 1999, 40, 1419-1422.
26. 4 was observed. This is in agreement with another report: Cox, C. D.; Malpass, J. R.; Gordon, J.; Rosen, A. J. Chem. Soc., Perkin Trans. 1 2001, 2372-2379.
27. Paquette, L. A.; Brand, S.; Behrens, C. J. Org. Chem. 1999, 64, 2010-2025.
28. The yield was not improved when the reaction was carried out with low-temperature addition (-78 °C).
29. Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611.
30. For Tebbe's reagent and ketone/ester chemoselectivity, see: (a) Pine, S. H.; Pettit, R. J.; Geib, G. D.; Cruz, S. G.; Gallego, C. H.; Tijerina, T.; Pine, R. D. J. Org. Chem. 1985, 50, 1212-1216. (b) Magnus, P.; Mugrage, B.; Deluca, M. R.; Cain, G. A. J. Am. Chem. Soc. 1990, 112, 5220-5230.
31. For Tebbe's reagent and ketone/ester chemoselectivity, see: (a) Pine, S. H.; Pettit, R. J.; Geib, G. D.; Cruz, S. G.; Gallego, C. H.; Tijerina, T.; Pine, R. D. J. Org. Chem. 1985, 50, 1212-1216. (b) Magnus, P.; Mugrage, B.; Deluca, M. R.; Cain, G. A. J. Am. Chem. Soc. 1990, 112, 5220-5230.
32. Cossy, J.; Cases, M.; Pardo, D. G. Tetrahedron 1999, 55, 6153-6166.
33. Lombardo, L. Tetrahedron Lett. 1982, 23, 4293-4296.
34. The quality of the zinc dust used had an impact on the reaction outcome. It is recommended to use only fresh zinc dust.
35. Brown, H. C.; Kanth, J. V. B.; Zaidlewicz, M. Tetrahedron 1999, 55, 5991-6000.
36. Burgess, K.; Donk, A. van der; Westcott, S. A.; Marder, T.B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350-9359.
37. For a recent review on transition metal catalyzed hydroboration, see: Beletskaya, I.; Pelter, A. Tetrahedron 1997, 53, 4957-5026.
38. 2/MeOH, EtOH/toluene, dioxane/heptanes.
39. Prashad, M.; Lu, Y.; Kim, H.-Y.; Hu, B.; Repic, O.; Blacklock, T. J. Synth. Commun. 1999, 29, 2937-2942.
40. Honoré, T.; Nielsen, M. Neurosci. Lett. 1995, 54, 27-32.
41. Braitman, D. J.; Coyle, J. T. Neuropharmacology 1987, 26, 1247-1251.
42. Bunch, L.; Johansen, T. H.; Bráuner-Osborne, H.; Stensbøl, T. B.; Johansen, T. N.; Krogsgaard-Larsen, P.; Madsen, U. Biorg. Med. Chem. 2001, 9, 875-879.
43. Sills, M. A.; Fagg, G.; Pozza, M.; Angst, C.; Brundish, D. E.; Hurt, S. D.; Wilusz, E. J.; Williams, M. Eur. J. Pharmacol. 1991, 192, 19-24.
44. Bráuner-Osborne, H.; Slok, F. A.; Skjærbæk, N.; Ebert, B.; Sekiyama, N.; Nakanishi, S.; Krogsgaard-Larsen, P. J. Med. Chem. 1996, 39, 3188-3194.
45. Sonnenberg, J. D.; Koch, H. P.; Willis, C. L.; Bradbury, F.; Daeuenhauer, D.; Bridges, R. J.; Chamberlin, A. R. Bioorg. Med. Chem. Lett. 1996, 6, 1607-1612.
46. Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am. Chem. Soc. 2000, 122, 7936-7943.