New 1H-Pyrazole-Containing Polyamine Receptors Able to Complex L-Glutamate in Water at Physiological pH Values

Journal of the American Chemical Society

Volumn 126, Issue 3, 2004, Pages 823-833

  Miranda, Carlos ^a   Escartí, Francisco ^b   Lamarque, Laurent ^a   Yunta, María J R ^c   Navarro, Pilar ^a   García España, Enrique ^b   Jimeno, M Luisa ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b UNIVERSITY OF VALENCIA   (Spain)

^c UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; AROMATIC COMPOUNDS; COMPLEXATION; HYDROGEN BONDS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH EFFECTS; PHYSIOLOGY; SYNTHESIS (CHEMICAL);

POTENTIOMETRY;

ORGANIC POLYMERS;

13,26 DIBENZYL 3,6,9,12,13,16,19,22,25,26 DECAAZATRICYCLO[22.2.1.1 11,14]OCTACOSA 1(27),11,14(28),24 TETRAENE; 3,6,9,12,13,16,19,22,25,26 DECAAZATRICYCLO[22.2.1.1 11,14]OCTACOSA 1(27),11,14(28),24 TETRAENE; 3,9,12,13,16,22,25,26 OCTAAZATRICYCLO[22.2.1.1 11,14]OCTACOSA 1(27),11,14(28),24 TETRAENE; 6,19 DIBENZYL 3,6,9,12,13,16,19,22,25,26 DECAAZATRICYCLO[22.2.1.1 11,14]OCTACOSA 1(27),11,14(28),24 TETRAENE; 6,19 DIOCTYL 3,6,9,12,13,16,19,22,25,26 DECAAZATRICYCLO[22.2.1.1 11,14]OCTACOSA 1(27),11,14(28),24 TETRAENE; 6,19 DIPHENETHYL 3,6,9,12,13,16,19,22,25,26 DECAAZATRICYCLO[22.2.1.1 11,14]OCTACOSA 1(27),11,14(28),24 TETRAENE; BENZYL DERIVATIVE; CATION; GLUTAMIC ACID; HETEROCYCLIC COMPOUND; MACROCYCLIC COMPOUND; NITROGEN; OCTYLAMINE; PHENETHYLAMINE; POLYAMINE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; HYDROGEN BOND; MEASUREMENT; MOLECULAR MODEL; MOLECULAR RECOGNITION; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; POTENTIOMETRY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE;

BIOMIMETIC MATERIALS; GLUTAMIC ACID; HYDROGEN-ION CONCENTRATION; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; POLYAMINES; POTENTIOMETRY; PYRAZOLES; RECEPTORS, GLUTAMATE; WATER;

EID: 1642494615     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035671m     Document Type: Article

References (63)

1. Jane, D. E. In Medicinal Chemistry into the Millenium; Campbell, M. M., Blagbrough, I. S., Eds.; Royal Society of Chemistry: Cambridge, 2001; pp 67-84.
2. (a) Standaert, D. G.; Young, A. B. In The Pharmacological Basis of Therapeutics; Hardman, J. G., Goodman Gilman, A., Limbird, L. E., Eds.; McGraw-Hill: New York, 1996; Chapter 22, p 503.
3. (b) Fletcher, E. J.; Loge, D. In An Introduction to Neurotransmission in Health and Disease; Riederer, P., Kopp, N., Pearson, J., Eds.; Oxford University Press: New York, 1990; Chapter 7, p 79.
4. Michaelis, E. K. Prog. Neurobiol. 1998, 54, 369-415.
5. Olney, J. W. Science 1969, 164, 719-721.
6. Green, J. G.; Greenamyre, J. T. Prog. Neurobiol. 1996, 48, 613-63.
7. Bräun-Osborne, H.; Egebjerg, J.; Nielsen, E. O.; Madsen, U.; Krogsgaard-Larsen, P. J. Med. Chem. 2000, 43, 2609-2645 and references therein.
8. (a) Shaw, P. J.; Ince, P. G. J. Neurol. 1997, 244 (Suppl 2), S3-S14.
9. (b) Plaitakis, A.; Fesdjian, C. O.; Shashidharan, P. CNS Drugs 1996, 5, 437-456.
10. Frantz, A.; Smith, A. Nat. Rev. Drug Dicovery 2003, 2, 9.
11. Rebek, J., Jr.; Askew, B.; Nemeth, D.; Parris, K. J. Am. Chem. Soc. 1987, 109, 2432-2434.
12. Seel, C.; de Mendoza, J. In Comprehensive Supramolecular Chemistry; Vogtle, F., Ed.; Elsevier Science: New York, 1996; Vol. 2, p 519.
13. (a) Sessler, J. L.; Sanson, P. I.; Andrievesky, A.; Kral, V. In Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., García-España, E., Eds.; John Wiley & Sons: New York, 1997; Chapter 10, pp 369-375.
14. (b) Sessler, J. L.; Andrievsky, A.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1997, 119, 9385-9392.
15. Fitzmaurice, R. J.; Kyne, G. M.; Douheret, D.; Kilburn, J. D. J. Chem. Soc., Perkin Trans. 1 2002, 7, 841-864 and references therein.
16. Rossi, S.; Kyne, G. M.; Turner, D. L.; Wells, N. J.; Kilburn, J. D. Angew. Chem., Int. Ed. 2002, 41, 4233-4236.
17. Aït-Haddou, H.; Wiskur, S. L.; Lynch, V. M.; Anslyn, E. V. J. Am. Chem. Soc. 2001, 123, 11296-11297.
18. Hosseini, M. W.; Lehn, J.-M. J. Am. Chem. Soc. 1982, 104, 3525-3527.
19. (a) Hosseini, M. W.; Lehn, J.-M. Helv. Chim. Acta 1986, 69, 587-603.
20. (b) Heyer, D.; Lehn, J.-M. Tetrahedron Lett. 1986, 27, 5869-5872.
21. (a) Alfonso, I.; Dietrich, B.; Rebolledo, F.; Gotor, V.; Lehn, J.-M. Helv. Chim. Acta 2001, 84, 280-295.
22. (b) Alfonso, I.; Rebolledo, F.; Gotor, V. Chem.-Eur. J. 2000, 6, 3331-3338.
23. Lamarque, L.; Navarro, P.; Miranda, C.; Arán, V. J.; Ochoa, C.; Escartí, F.; García-España, E.; Latorre, J.; Luis, S. V.; Miravet, J. F. J. Am. Chem. Soc. 2001, 123, 10560-10570.
24. Foces-Foces, C.; Echevarria, A.; Jagerovic, N.; Alkorta, I.; Elguero, J. ; Langer, U.; Klein, O.; Minguet-Bonvehí, H.-H. J. Am. Chem. Soc. 2001, 123, 7898-7906.
25. Sussman, J. L.; Harel, M.; Frolow, F.; Oefner, C.; Goldman, A.; Toker, L.; Silman, I. Science 1991, 253, 872-879.
26. Dougherty, D. A.; Stauffer, D. A. Science 1990, 250, 1558-1560.
27. (a) Sutcliffe, M. J.; Smeeton, A. H.; Wo, Z. G.; Oswald, R. E. Faraday Discuss. 1998, 111, 259-272.
28. (b) Kearney, P. C.; Mizoue, L. S.; Kumpf, R. A.; Forman, J. E.; McCurdy, A.; Dougherty, D. A. J. Am. Chem. Soc. 1993, 115, 9907-9919.
29. (c) Bräuner-Osborne, H.; Egebjerg, J.; Nielsen, E.; Madsen, U.; Krogsgaard-Larsen, P. J. Med. Chem. 2000, 43, 2609-2645.
30. (d) Zacharias, N.; Dougherty, D. A. Trends Pharmacol. Sci. 2002, 23, 281-287.
31. (e) Hu, J.; Barbour, L. J.; Gokel, G. W. J. Am. Chem. Soc. 2002, 124, 10940-10941.
32. Arán, V. J.; Kumar, M.; Molina, J.; Lamarque, L.; Navarro, P.; García-España, E.; Ramírez, J. A.; Luis, S. V.; Escuder, B. J. Org. Chem. 1999, 64, 6137-6146.
33. (a) Yuen Ng, C.; Motekaitis, R. J.; Martell, A. E. Inorg. Chem. 1979, 18, 2982-2986.
34. (b) Anelli, P. L.; Lunazzi, L.; Montanari, F.; Quici, S. J. Org. Chem. 1984, 49, 4197-4203.
35. (a) Martell, E.; Smith, R. M. Critical Stability Constants; Plenum: New York, 1975.
36. (b) Motekaitis, R. J. NIST Critically Selected Stability Constants of Metal Complexes Database; NIST Standard Reference Database, version 4, 1997.
37. Escartí, F.; Miranda, C.; Lamarque, L.; Latorre, J.; García-España, E.; Kumar, M.; Arán, V. J.; Navarro, P. Chem. Commun. 2002, 9, 936-937.
38. (a) Bianchi, A.; García-España, A. J. Chem. Educ. 1999, 12, 1725-1732.
39. (b) Aguilar, J. A.; Celda, B.; García-España, E.; Luis, S. V.; Martínez, M.; Ramírez, J. A.; Soriano, C.; Tejero, B. J. Chem. Soc., Perkin Trans. 2 2000, 7, 1323-1328.
40. Urban, J. J.; Cronin, C. W.; Roberts, R. R.; Famini, G. R. J. Am. Chem. Soc. 1997, 119, 12292-12299.
41. Hobza, P.; Kabelac, M.; Sponer, J.; Mejzlik, P.; Vondrasek, J. J. Comput. Chem. 1997, 18, 1136-1150.
42. Cornell, W. D.; Cieplak, P.; Bayly, C. I.; Gould, I. R.; Merz, K. M., Jr.; Ferguson, D. M.; Spelmeyer, D. C.; Fox, T.; Caldwell, J. W.; Kollman, P. A. J. Am. Chem. Soc. 1995, 117, 5179-5197.
43. Hyperchem 6.0 (Hypercube Inc.).
44. (a) Fox, T.; Scanlan, T. S.; Kollman, P. A. J. Am. Chem. Soc. 1997, 119, 11571-11577.
45. (b) Grootenhuis, P. D.; Kollman, P. A. J. Am. Chem. Soc. 1989, 111, 2152-2158.
46. (c) Moyna, G.; Hernandez, G.; Williams, H. J.; Nachman, R. J.; Scott, A. I. J. Chem. Inf. Comput. Sci. 1997, 37, 951-956.
47. (d) Boden, C. D. J.; Patenden, G. J. Comput.-Aided Mol. Des. 1999, 13, 153-166.
48. http://www.amber.ucsf.edu/amber.
49. Hopfinger, A. J.; Pearlstein, R. A. J. Comput. Chem. 1984, 5, 486-499.
50. Glennon, T. M.; Zheng, Y.-J.; Le Grand, S. M.; Shutzberg, B. A.; Merz, K. M., Jr. J. Comput. Chem. 1994, 15, 1019-1040.
51. Wang, J.; Kollman, P. A. J. Am. Chem. Soc. 1998, 120, 11106-11114.
52. Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C.; Alagona, G.; Profeta, S., Jr.; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765-784.
53. Covington, A. K.; Paabo, M.; Robison, R. A.; Bates, R. G. Anal. Chem. 1968, 40, 700-706.
54. (a) Andrés, A.; Burguete, M. I.; García-España, E.; Luis, S. V.; Miravet, J. F.; Soriano, C. J. Chem. Soc., Perkin Trans. 2 1993, 4, 749-755.
55. (b) Bianchi, A.; Escuder, B.; García España, E.; Luis, S. V.; Marcelino, V.; Miravet, J. F.; Ramírez, J. A. J. Chem. Soc., Perkin Trans. 2 1994, 6, 1253-1259.
56. (c) Andrés, A.; Bazzicaluppi, C.; Bianchi, A.; García España, E.; Luis, S. V.; Miravet, J. F.; Ramírez, J. A. J. Chem. Soc., Dalton Trans. 1994, 20, 2995-3004.
57. (d) Aguilar, J. A.; García-España, E.; Guerrero, J. A.; Llinares, J. M.; Ramírez, J. A.; Soriano, C.; Luis, S. V.; Bianchi, A.; Ferrini, L.; Fusi, V. J. Chem. Soc., Dalton Trans. 1996, 2, 239-246.
58. García-España, E.; Ballester, M. J.; Lloret, F.; Moratal, J.-M.; Faus, J.; Bianchi, A. J. Chem. Soc., Dalton Trans. 1988, 2, 101-104.
59. Fontanelli, M.; Micheloni, M. Proceedings of the 1st Spanish-Italian Congress on Thermodynamics of Metal Complexes; Diputación de Castellón: Peñíscola (Castellón), España, 3-6 Junio 1990.
60. (a) Gran, G. Analyst (London) 1952, 77, 661.
61. (b) Rossoti, F. J. C.; Rossoti, H. J. Chem. Educ. 1965, 42, 375-378.
62. Gans, P.; Sabatini, A.; Vacca, A. Talanta 1996, 43, 1739-1753.
63. Gans, P. Program to determine the distribution of species in multiequilibria systems from the stability constants and mass balance equations.