Cyclobisintercaland Macrocycles: Synthesis and Physicochemical Properties of Macrocyclic Polyamines Containing Two Crescent-Shaped Dibenzophenanthroline Subunits

Journal of Organic Chemistry

Volumn 62, Issue 16, 1997, Pages 5458-5470

  Baudoin, Olivier ^a   Teulade Fichou, Marie Paule ^a   Vigneron, Jean Pierre ^a   Lehn, Jean Marie ^a  

^a Paris Sciences et Lettres   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000758185     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970496b     Document Type: Article

References (89)

1. Saenger, W. Principles of nucleic acid structures; Springer-Verlag: New York, 1984; pp 132-133.
2. (a) Quigley, G. J.; Ughetto, G.; Van Der Marel, G. A.; Van Boom, J. H.; Wang, A. H.-J.; Rich, A. Science 1986, 232, 1255.
3. (b) Kennard, O.; Hunter, W. N. Angew. Chem., Int. Ed .Engl. 1991, 30, 1254.
4. (c) Brown, D. R.; Kurz, M.; Kerans, D. R.; Hsu, V. L. Biochemistry 1994, 33, 651.
5. (d) Pindur, U.; Haber, M.; Sattler, K. J. Chem. Educ. 1993, 70, 263.
6. (e) Wilson, D. W.; Ratmeyer, L.; Zhao, M.; Strekowski, L.; Boykin D. Biochemistry 1993, 32, 4098.
7. (a) Sanders, J. M.; Hunter, C. A. J. Am. Chem. Soc. 1990, 112, 5525.
8. (b) Hunter, C. A Angew. Chem., Int. Ed. Engl. 1993, 32, 1584.
9. (c) Cozzi, F.; Cinquini, M.; Annunziata, R.; Dwyer, T.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 5729.
10. (d) Cozzi, F.; Cinquini, M.; Annunziata, R.; Siegel J. S. J. Am. Chem. Soc. 1993, 115, 5330.
11. (e) Cozzi, F.; Ponzini, F.; Annunziata, R.; Cinquini, M.; Siegel J. S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1019.
12. (a) Guckian, K. M.; Schweitzer, B. A ; Ren, R. X.-F.; Sheils, C. J.; Paris, P. L.; Tahmassebi, D.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 8182 and references cited therein.
13. (b) Ren, X.-F.; Schweitzer, B. A.; Sheils, C. J.; Kool, E. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 743.
14. (a) Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1990, 29, 245.
15. (b) Lin, K.-Y.; Jones R. J.; Matteucci, M. J. Am. Chem. Soc. 1995, 117, 3873 and references cited therein.
16. (a) Zimmerman, S. C. Top. Curr. Chem. 1993, 165, 71.
17. (b) Hamilton, A. Adv. Supramol. Chem. 1991, 1, 1.
18. (c) Hosseini, M. W.; Blacker, A. J.; Lehn, J.-M. J. Am. Chem. Soc. 1990, 112, 3896.
19. (d) Galan, A.; Pueyo, E.; Salmeron, A.; de Mendoza, J. Tetrahedron Lett. 1991, 32, 1827.
20. (e) Schneider, H. J.; Blatter, T.; Palm, B.; Pfinstag, U.; Rüdiger, V.; Theis, I. J. Am. Chem. Soc. 1992, 114, 7704.
21. (f) Rotello, V. M.; Viani, E. A.; Deslongchamps, G.; Murray, B. A.; Rebek, J., Jr. J. Am. Chem. Soc. 1993, 115, 797.
22. (g) Shionoya, M.; Ikeda, T.; Kimura, E.; Shiro, M. J. Am. Chem. Soc. 1994, 116, 3848.
23. (a) Claude, S.; Lehn, J.-M.; Schmidt, F.; Vigneron, J.-P. J. Chem. Soc., Chem. Commun. 1991, 1182.
24. (b) Dhaenens M.; Lehn J.-M.; Vigneron J.-P. J. Chem. Soc., Perkin Trans. 2 1993, 1379 and references cited therein.
25. (c) Teulade-Fichou M.-P.; Vigneron, J.-P.; Lehn, J.-M. Supramol. Chem. 1995, 5, 139.
26. (d) Cudic, P.; Zinic, M.; Tomisic, V.; Simeon, Vl.; Vigneron, J.-P.; Lehn, J.-M, J. Chem. Soc., Chem. Commun. 1995, 1073.
27. (a) Constant, J. F.; Fahy, J.; Lhomme, J. Tetrahedron Lett. 1987, 16, 1777.
28. (b) Furuta, H.; Magda, D.; Sessler, J. L. J. Am. Chem. Soc. 1991, 113, 978.
29. (c) Schall, O. F.; Gokel, G. W. J. Am. Chem. Soc. 1994, 116, 6089.
30. (d) Gokel G. W.; Schall, O. F. J. Org. Chem. 1996, 61, 1449.
31. Branda, N.; Kurz, G.; Lehn, J.-M. J. Chem. Soc., Chem. Commun. 1996, 2443.
32. Jeffrey, G. A.; Saenger, W. Hydrogen Bonding in Biological Structures; Springer-Verlag: New York, 1991; p 247.
33. (a) Edwards, E. L.; Ratliff, P. R. L.; Gray, D. M. Biochemistry 1990, 29, 1417.
34. (b) Holbrook, S. R.; Cheong, C.; Tinoco, I.; Kim, S.-H. Nature 1991, 353, 579.
35. (c) Nikonowicz, E. P.; Gorenstein, D. G. Biochemistry 1990, 29, 8845.
36. (d) Felsenfeld, G.; Miles, H. T. Annu. Rev. Biochem. 1967, 36, 407.
37. (e) Htun, H.; Dahlberg J. E. Science 1989, 243, 1571.
38. (f) Sen, D.; Gilbert, W. Nature 1988, 334, 364.
39. (g) Sundquist, W. I.; Klug, A. Nature 1989, 342, 825.
40. (h) Gehring K.; Leroy, J.-L.; Guéron, M. Nature 1993, 363, 561.
41. (a) Le Doan, T.; Hélène, C. Nucleic Acids Res. 1987, 15, 7749.
42. (b) Moser, H. E.; Dervan, P. B. Science 1987, 238, 645.
43. (c) Strobel, S. A.; Dervan, P. B. Science 1990, 249, 73.
44. (d) Thuong, N. T.; Hélène, C. Angew. Chem., Int. Ed. Engl. 1993, 32, 666.
45. (e) Hélène, C. Antisense Research and applications; Cooke, S. T., Lebleu, B., Eds.; CRC Press, Boca Ratan, FL, 1993; p 375.
46. Le, S.-Y.; Pattabiraman, N.; Maizel, J. V., Jr. Nucleic Acids Res. 1994, 22, 3966.
47. Lee, J. S.; Latimer, L. J. P.; Hampel, K. J. Biochemistry 1993, 32, 5591.
48. (a) Escudé, C.; Nguyen, C. H.; Mergny, J. L.; Sun, J.-S.; Bisagni, E.; Garestier, T.; Hélène, C. J. Am. Chem. Soc. 1995, 177, 10212.
49. (b) Escudé, C.; Mohammadi, S.; Sun, J.-S; Nguyen, C. H.; Bisagni, E.; Liquier, J.; Taillandier E.; Garestier, T.; Héiène, C. Chem. Biol. 1996, 3, 57.
50. (a) Haq, I.; Ladbury, J. E.; Chowdhry, B. Z.; Jenkins, T. E. J. Am. Chem. Soc. 1996, 118, 10693.
51. (b) Fox, K. R.; Polucci, P.; Jenkins, T. C.; Neidle, S. Proc Natl. Acad. Sci. U.S.A. 1995, 92, 7887.
52. Acheson, R. M. Acridines, The Chemistry of Heterocyclic Compounds; John Wiley & Sons, Interscience: 1973; Vol. 9, p 563.
53. (a) Labana, S. S.; Labana, L. L. Chem. Rev. 1967, 67, 1.
54. (b) Potts, G. D.; Jones, W.; Bullock, J. F.; Andrews, S. J.; Maginn, S. J. J. Chem. Soc., Chem. Commun. 1994, 2565.
55. (c) Manabe, K.; Kusabayashi, S; Yokoyama, M. Chem. Lett. 1987, 609.
56. (a) Niementowski, S. Chem. Ber. 1906, 39, 385.
57. (b) Ullmann, F.; Maag, R. Chem. Ber. 1907, 40, 2515.
58. (c) Badger G. M.; Pettit R. J. Chem. Soc. 1952, 1874.
59. (d) Dali, H. M.; Gogte V. N.; Mullick, G. B.; Tilak, B. D. Indian J. Chem. 1974, 12, 1230.
60. (e) Belser, P.; Zelewsky, V. A. Helv. Chim. Acta 1980, 63, 1675.
61. (f) Hellwinkel, D.; Ittemann, P. Liebigs Ann. Chem. 1985, 1501.
62. (a) Thummel, R. P. Synlett 1992, 1, 1.
63. (b) Hung, C.-Y.; Wang, T.-L.; Shi, Z.; Thummel, R. P. Tetrahedron 1994, 50, 10685.
64. For a review, see: Fu, P. P.; Harvey, R. G. Chem. Rev. 1978, 4, 317.
65. (a) Rieke, R. D.; Rhyne, D. L. J. Org. Chem. 1979, 44, 3445.
66. (b) Gauthier S.; Fréchet, J. M. J. Synthesis 1987, 383.
67. (c) Carrasco, R.; Pellon, R. F., Elguero, J.; Goya, P.; Paèz, J. A. Synth. Comm. 1989, 11&12, 2077.
68. (d) Pellon, R. F.; Carrasco, R.; Rodes, L. Synth. Commun. 1993, 23, 1447.
69. Chandler, C. J.; Deady, L. W.; Reiss, J. A. J. Heterocycl. Chem. 1981, 18, 599.
70. Cesario, M.; Paris, T.; Vigneron, J.-P.; Lehn, J.-M. J. Inclusion. Phenom. Mol. Recognit. Chem., in press.
71. (a) Adams, H.; Bailey, N. A.; Fenton, D. E.; Good, R. J.; Moody, R.; Rodriguez de Barbarin, C. O. J. Chem. Soc., Dalton Trans. 1987, 207.
72. (b) Adams, H.; Bailey, N. A.; Fenton, D. E.; Hempstead, P. D.; Westwood, G. P. J. Inclusion. Phenom. Mol. Recognit. Chem. 1991, 11, 63.
73. (c) Rockcliffe, D. A.; Martell, A. E.; Reibenspies, J. H. J. Chem. Soc., Dalton Trans. 1996, 167.
74. (d) Adams, H.; Bailey, N. A.; Bertrand, P.; Collinson, S. R.; Fenton, D. E.; Kitchen, S. J. J. Chem. Soc., Dalton Trans. 1996, 1181.
75. Baldwin J. E., J. Chem. Soc., Chem. Commun. 1976, 734.
76. (a) Badger, G. M.; Walker, I. S. J. Chem .Soc. 1956, 122.
77. (b) Henry, M. S.; Hoffman, M. Z. J. Phys. Chem. 1979, 83, 618.
78. (c) Armaroli, N.; De Cola, L.; Balzani., V.; Sauvage, J.-P.; Dietrich-Buchecker, C. O.; Kern, J.-M.; Sauvage, J.-P. J. Chem. Soc., Faraday Trans. 1992, 88, 553.
79. (d) Dietrich-Buchecker, C. O.; Sauvage, J.-P; Armaroli, N.; Ceroni, P.; Balzani., V. New J. Chem. 1996, 20, 801.
80. (e) Perkampus, H.-H.; Köhler, H. Z. Elektrochem. 1960, 64, 365.
81. (a) De Silva, A. P.; De Silva, S. A. J. Chem. Soc, Chem. Commun. 1986, 1709.
82. (b) Czarnik, A. W. Acc. Chem. Res. 1994, 27, 302.
83. (a) Castellan, A.; Desvergne, J.-P.; Bouas-Laurent, H. Nouv. J. Chem. 1979, 3, 231.
84. (b) Hinschberger, J.; Desvergne, J.-P.; Bouas-Laurent, H.; Marsau, P. J. Chem. Soc., Perkin Trans. 2 3990, 93.
85. (c) Bouas-Laurent, H.; Castellan, A.; Daney, M.; Desvergne, J.-P.; Guinand, P.; Marsau, P. Riffaud, M. H. J. Am. Chem. Soc. 1986, 108, 315.
86. (d) Misumi, S.; Otsubo, T. Acc. Chem. Res. 1978, 11, 251.
87. De Schryver, F. C.; Collart, P.; Vandendriessche, J.; Goedeweeck, R.; Swinnen, A.; Van der Auweraer, M. Acc. Chem. Res. 1987, 20, 159.
88. Pilch, D. S.; Martin, M.-T.; Nguyen, C. H.; Sun, J.-S; Bisagni, E.; Garestier, T.; Hélène, C. J. Am. Chem. Soc. 1993, 115, 9942.
89. Slama-Schwok, A.; Teulade-Fichou, M.-P.; Vigneron, J.-P.; Lehn, J.-M.; Taillandier, E. J. Am. Chem. Soc. 1995, 117, 6822.