Neutral molecule receptor systems using ferrocene's 'atomic ball bearing' character as the flexible element

Journal of the American Chemical Society

Volumn 119, Issue 7, 1997, Pages 1609-1618

  Li, Chensheng ^a   Medina, Julio C ^a   Maguire, Glenn E M ^b   Abel, Ernesto ^b   Atwood, Jerry L ^c   Gokel, George W ^b  

^a UNIVERSITY OF MIAMI   (United States)

^b UNIVERSITY OF MISSOURI   (United States)

^c WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FERROCENE DERIVATIVE;

ARTICLE; COMPLEX FORMATION; DRUG SYNTHESIS; MODEL; NUCLEAR MAGNETIC RESONANCE; RECEPTOR BINDING;

EID: 0030988092     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9600284     Document Type: Article

References (69)

1. (a) Suckling, C. J. Enzyme Chemistry: Impact and Implications, 2nd ed.; Chapman and Hall: London, New York, 1990.
2. (b) Dugas, H. Bioorganic Chemistry: A Chemical Approach to Enzyme Action, 2nd ed.; Springer-Verlag: New York, 1989.
3. (c) Krogsgard-Larsen, P. A Textbook of Drug Design and Development; Harwood Academic: Switzerland, 1991; pp 419-28.
4. (a) Hamilton, A. D. Adv. Supramol. Chem. 1992, 1, 1.
5. (b) Muehldorf, A.; Engen, D.; Warner, J.; Hamilton, A. J. Am. Chem. Soc. 1988, 110, 6561-2.
6. (c) Kelly, T. R.; Maquire, P. J. Am. Chem. Soc. 1987, 109, 6549-51.
7. (d) Kelly, T. R.; Bilodeau, M. T.; Bridger, G. J.; Zhao, C. Tetrahedron. Lett. 1989, 30, 2485-8.
8. (e) Kelly, T. R.; Zhao, C.; Bridger, G. J. J. Am. Chem. Soc. 1989, 111, 3744-5.
9. (f) Kelly, T. R.; Maquire, M. P. J. Am. Chem. Soc. 1987, 109, 6549-51.
10. (g) Hamilton, A. D.; Van Engen, D. J. Am. Chem. Soc. 1987, 109, 5035.
11. Hosseini, M. W.; Lehn, J.-M.; Jones, K. C.; Plute, K. E.; Mertes, K. B.; Mertes, M. P. J. Am. Chem. Soc. 1989, 11, 6330-6335.
12. Zimmerman, S. C.; VanZyl, C. M.; Hamilton, G. S. J. Am. Chem. Soc. 1989, 111, 1373-81.
13. (a) Anslyn, E.; Breslow, R. J. Am. Chem. Soc. 1989, 111, 5973-5974.
14. (b) Anslyn, E.; Breslow, R. J. Am. Chem. Soc. 1989, 111, 8931-8932.
15. (c) Smith, J.; Ariga, K.; Anslyn, E. J. Am. Chem. Soc. 1993, 115, 362-364.
16. (d) Perreault, D. M.; Chen, X.; Anslyn, E. Tetrahedron 1995, 51, 353-362.
17. (a) Harmata, M.; Barnes, C. L. J. Am. Chem. Soc. 1990, 112, 5655-7.
18. (b) Harmata, M.; Elahmad, S.; Barnes, C. L.; Karra, S. R. J. Am. Chem. Soc. 1994, 116, 8392-3.
19. (a) Harriman, A., Kubo, Y., Sessler, J. L. J. Am. Chem. Soc. 1992, 114, 388-390.
20. (b) Sessler, J. L.; Cyr, M. J.; Burrell, A. K. Synlett 1991, 127-134.
21. Webb, T. H.; Suh, H.; Wilcox, C. S. J. Am. Chem. Soc. 1991, 113, 8554-5.
22. Ferguson, S. B.; Sandford, E. M.; Seward, E. M.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 5410-9. Diederich, F. Angew. Chem., Int. Ed. Engl. 1988, 27, 362-386. Smithrud, D. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 339-343.
23. Ferguson, S. B.; Sandford, E. M.; Seward, E. M.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 5410-9. Diederich, F. Angew. Chem., Int. Ed. Engl. 1988, 27, 362-386. Smithrud, D. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 339-343.
24. Ferguson, S. B.; Sandford, E. M.; Seward, E. M.; Diederich, F. J. Am. Chem. Soc. 1991, 113, 5410-9. Diederich, F. Angew. Chem., Int. Ed. Engl. 1988, 27, 362-386. Smithrud, D. B.; Diederich, F. J. Am. Chem. Soc. 1990, 112, 339-343.
25. Anelli, P.; Ashton, P.; Ballardini, R.; Balzani, V.; Delgado, M.; Gandofi, M.; Goodnow, T.; Kaifer, A.; Philip, D.; Pietraszkiewicz, Prodi, L.; Reddington, M.; Slawin, A.; Spencer, N.; Stoddart, F.; Vincent, C.; Williams, D. J. Am. Chem. Soc. 1992, 114, 93-218.
26. (a) Rebek, J., Jr.; Askew, B.; Islam, N.; Killoran, M.; Nemeth, D.; Wolak, R. J. Am. Chem. Soc. 1985, 107, 6736-6738.
27. (b) Rebek, J., Jr.; Nemeth, D., J. Am. Chem. Soc., 1985, 107, 6738-9.
28. (c) Rebek, J., Jr.; Marshall, L.; Walock, R.; Parris, K.; Killoran, M.; Askew, B.; Nemeth, D.; Islam, N.; J. Am. Chem. Soc. 1985, 107, 7476-7481.
29. (d) Rebek, J., Jr.; Nemeth, D. J. Am. Chem. Soc. 1986, 108, 5637-5638.
30. (f) Rebek, J., Jr.; Duff, R. J.; Gordon, W. E.; Parris, K. J. Am. Chem. Soc. 1986, 108, 6068-6069.
31. (g) Rebek, J., Jr.; Askew, B.; Ba; P.; Buhr, C.; Costero, A.; Jones, S.; Williams, K. J. Am. Chem. Soc. 1987, 109, 6866-6867.
32. (h) Rebek, J., Jr.; Askew, B.; Ballester, P.; Buhr, C.; Jones, S.; Nemeth, D.; Willams, K. J. Am. Chem. Soc. 1987, 109, 5033-5035.
33. (i) Rebek, J., Jr.; Askew, B.; Ballester, P.; Doa, M. J. Am. Chem. Soc. 1987, 109, 4119-4120.
34. (j) Rebek, J., Jr.; Askew, B.; Killoran, M.; Nemeth, D.; Li, F.-T. J. Am. Chem. Soc. 1987, 109, 2432-2434.
35. (k) Rebek, J.. Jr, Science 1987, 235, 1478-1484.
36. (l) Rebek, J., Jr.; Williams, K.; Parris, K.; Ballester, P.; Jeong, K-S. Angew. Chem., Int. Ed. Engl. 1987, 26, 1244.
37. Lindsey, J. S.; Kearney, P. C.; Duff, R. J.; Tjivikua, P. T.; Rebek, J., Jr. J. Am. Chem. Soc. 1988, 110, 6575-6577.
38. (n) Huff, J. B.; Askew, B.; Duff, R. J.; Rebek J., Jr. J. Am. Chem. Soc. 1988, 5908-5909.
39. (o) Marshall, L.; Parris, K.; Rebek, J., Jr. J. Am. Chem. Soc. 1988, 110, 5092-5093.
40. (p) Askew, B.; Ballester, P.; Bunr, C.; Jeong, K.; Jones, S.; Parris, K.; Rebek, Jr., J. J. Am. Chem. Soc. 1989, 111, 1082.
41. Kemp, D. S. J. Org. Chem., 1981, 46, 5140.
42. Medina, J. C.; Li, C.; Bott, S. G.; Atwood, J. L.; Gokel, G. W. J. Am. Chem. Soc. 1991, 113, 366.
43. Jorgensen, W. L.; Boudon, S.; Nguyen, T. B. J. Am. Chem. Soc. 1989, 111, 755.
44. Pascal, R. A., Jr.; Ho, D. M. J. Am. Chem. Soc. 1993, 115, 8507.
45. Duffy, E. M.; Jorgensen, W. L. J. Am. Chem. Soc. 1994, 116, 6337.
46. Luke, W. D.; Streitwieser, A., Jr. J. Am. Chem. Soc. 1981, 103, 3241 and references therein.
47. (a) Medina, J. C.; Gay, I.; Chen, Z.; Echegoyen, L.; Gokel, G. W. J. Am. Chem. Soc. 1991, 113, 365-366.
48. (b) Medina, J. C.; Goodnow, T. T.; Rojas, M. T.; Atwood, J. L.; Lynn, B. C.; Kaifer, A. E.; Gokel, G. W. J. Am. Chem. Soc. 1992, 114, 10583-10595.
49. (c) Rojas, M. T.; Medina, J. C.; Gokel, G. W.; Kaifer, A. K.; Supramol. Chem. 1993, 2, 5-9.
50. Yamakawa, K.; Ochi, H.; Arakawa, K. Chem. Pharm. Bull. 1963, 11, 905.
51. (a) Nesmeyanov, A. N.; Reutov, O. A. Dokl. Akad. Nauk SSSR 1958, 120, 1267; Chem. Abstr. 1959, 53, 1292.
52. (a) Nesmeyanov, A. N.; Reutov, O. A. Dokl. Akad. Nauk SSSR 1958, 120, 1267; Chem. Abstr. 1959, 53, 1292.
53. (b) Ban, K.; Saegusa, T.; Furukawa J.; Kogyo Kagaku Zasshi 1966, 69, 148; Chem. Abstr. 1966, 65, 7287.
54. (b) Ban, K.; Saegusa, T.; Furukawa J.; Kogyo Kagaku Zasshi 1966, 69, 148; Chem. Abstr. 1966, 65, 7287.
55. Schaaf, R. L. J. Org. Chem. 1962, 27, 107, 111.
56. Nesmeyanov, A. N.; Reutov, O. A. Dokl. Akad. Nauk. SSSR 1957, 115, 518.
57. Ashton, P. R.; Claessens, C. G.; Hayes, W.; Menzer, S.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1995, 34, 1862.
58. Herceg, M.; Weiss, R. Bull. Soc. Chim. Fr. 1972, 549.
59. Medina, J. C.; Goodnow, T. T.; Rojas, M. T.; Atwood, J. L.; Lynn, B. C.; Kaifer, A. E.; Gokel, G. W. J. Am. Chem. Soc. 1992, 114, 10583-10595.
60. Li, C.; Tsesarskaja, M.; Gokel, G. W. Supramol. Chem. 1995, 6, 79.
61. (a) Kerwin, J. F.; Danishefsky, S. Tetrahedron. Lett. 1982, 23, 3739-42.
62. (b) Danishefsky, S.; Langer, M. E.; Vogel, C. Tetrahedron Lett. 1985, 26, 5983-6.
63. Cox, B. G. Schneider, H.; Stroka, J. J. Am. Chem. Soc. 1978, 100, 4746.
64. (a) Eadie, G. S. J. Biol. Chem. 1942, 146, 85.
65. (b) Hofstee, B. H. J. Nature 1959, 184, 1296.
66. Lineweaver, H.; Burke, D. J. Am. Chem. Soc. 1934, 56, 658.
67. Molecular models of ferrocene were constructed by drilling a center hole in each five-membered aromatic ring and then connecting two rings with a bolt. This permitted rotation about the long axis, and the separation of the bisecting planes of each cyclopentadienyl ring was only slightly larger than 3.25 Å.
68. Live, D.; Chan, S. I. J. Am. Chem. Soc. 1976, 98, 3769.
69. Hamilton, A. D. Adv. Supramol. Chem. 1990, 1, 1.