Syntheses of imidazole-acridine conjugates as ribonuclease A mimics

Tetrahedron Letters

Volumn 37, Issue 25, 1996, Pages 4417-4420

  Lorente, Antonio ^a   Espinosa, Juan Félix ^a   Fernández Saiz, Misericordia ^a   Lehn, Jean Marie ^b   Wilson, W David ^c   Zhong, Yi Yi ^c  

^a UNIVERSITY OF ALCALÁ   (Spain)

^b PSL Research University   (France)

^c GEORGIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVE; IMIDAZOLE DERIVATIVE; INTERCALATING AGENT; PROFLAVINE; RIBONUCLEASE A; TRANSFER RNA;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CONJUGATE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME SUBSTRATE COMPLEX; MOLECULAR RECOGNITION; RNA CLEAVAGE;

EID: 0029946227     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00843-X     Document Type: Article

References (28)

1. (a) Stern, M. K.; Bashkin, J. K.; Sall, E. D. J. Am. Chem. Soc. 1990, 112, 5357.
2. (b) Matsumoto, Y; Komiyama, M. J. Chem. Soc., Chem. Comm. 1990, 1050.
3. (c) Modak, A. S.; Gard, J. K.; Merriman, M. C.; Winkeler, K.A.; Bashkin, J. K.; Stern, M. K. J. Am. Chem. Soc. 1991, 113, 283.
4. (d) Morrow, J. R.; Buttrey, L. A.; Shelton, V. M.; Berback, K. A. J. Am. Chem. Soc. 1992, 114, 1903.
5. (e) Komiyama, M.; Matsumura, K.; Matsumoto, Y. J. Chem. Soc., Chem. Comm. 1992, 640.
6. (f) Morrow, J. R.; Shelton, V. M. New J. Chem. 1994, 18, 371.
7. (g) Matsumura, S.; Endo, M. Komiyama, M. J. Chem. Soc., Chem. Comm. 1994, 2019.
8. (h) Yashiro, M.; Ishikubo, A.; Komiyama, M. J. Chem. Soc., Chem. Comm. 1995, 1793.
9. (i) Irisawa, M.; Takeda, N.; Komiyama, M. J. Chem. Soc., Chem. Comm. 1995, 1221.
10. (j) Hashimoto, S.; Nakamura, Y. J. Chem. Soc., Chem. Comm. 1995, 1413.
11. (a) Yoshinari, K.; Yamazaki, K.; Komiyama, M. J. Am. Chem. Soc. 1991, 113, 5899.
12. (b) Polyamine-induced hydrolysis of apurinic sites in DNA and nucleosomes has been reported: Male, R.; Fosse, V. M.; Kleppe, K. Nucleics Acids Res. 1982, 10, 6305.
13. Barbier, B.; Brack, A. J. Am. Chem. Soc. 1988, 110, 6880.
14. Komiyama, M.; Inokawa, T.; Yoshinari, K. J. Chem. Soc., Chem. Comm. 1995, 77.
15. Wyckoff, H. W.; Tsernoglou, D.; Hanson, A. W.; Knox, J. R.; Lee, B.; Richards, F. M. J. Biol. Chem. 1970, 245, 305.
16. Breslow, R. Acc. Chem. Res. 1991, 24, 317.
17. Tung, C-H.; Wei, Z.; Leibowitz, M. J.; Stein, S. Proc. Natl. Acad. Sci. USA 1992, 89, 7114.
18. (a) Shinozuka, K.; Shimizu, K.; Nakashima, Y.; Sawai, H. Bioorg. Med. Chem. Lett. 1994, 4, 1979.
19. (b) Lhomme reported the synthesis (Fkyerat, A.; Demeunynck, M.; Constant, J.-F.; Lhomme, J. Tetrahedron 1993, 49, 11237) and cleavage (Fkyerat, A.; Demeunynck, M.; Constant, J.-F.; Michon, P.; Lhomme, J. J. Am. Chem. Soc. 1993, 115, 9952) of depurinated DNA by purineacridine hybrid molecules.
20. (b) Lhomme reported the synthesis (Fkyerat, A.; Demeunynck, M.; Constant, J.-F.; Lhomme, J. Tetrahedron 1993, 49, 11237) and cleavage (Fkyerat, A.; Demeunynck, M.; Constant, J.-F.; Michon, P.; Lhomme, J. J. Am. Chem. Soc. 1993, 115, 9952) of depurinated DNA by purineacridine hybrid molecules.
21. Podyminogin, M. A.; Vlassov, V. V; Giegé, R. Nucleic Acids Res. 1993, 21, 5950.
22. Totter, J. R.; Darby, W. J. Org. Synth. Coll. Vol. III 1955, 460.
23. Turner, R. A.; Huebner, C. F.; Scholz, C. R. J. Am. Chem. Soc. 1949, 71, 2801.
24. Kelly, J. L.; Miller, C. A.; McLean, E. W. J. Med. Chem. 1977, 20, 721.
25. 4 1783.8)
26. 13 615.3).
27. 2N-acridine), 6.54 (s, 2H, H-5 imidazole), 6.94-7.38 (m, 35H, 3H acridine, 2H imidazole and 30H Ph-H), 7.62 (d, 1H, J= 8.79 Hz, H-8 acridine), 7.72 (d, 1H, J= 1.1 Hz, H-4 acridine), 7.80 (d, 1H, J= 9.16 Hz, H-1 acridine), 8.49 (s, 1H, H-9 acridine).
28. 8 412.2).