Design and synthesis of novel thiazole-containing cross-linked polyamides related to the antiviral antibiotic distamycin

Journal of Organic Chemistry

Volumn 65, Issue 4, 2000, Pages 1102-1107

  Sharma, Sanjay K ^a   Tandon, Manju ^a   Lown, J William ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; CONGOCIDINE; DISTAMYCIN A; GYRASE INHIBITOR; THIAZOLE DERIVATIVE;

ARTICLE; CONCENTRATION RESPONSE; CROSS LINKING; DRUG SYNTHESIS; ENZYME INHIBITION; MOLECULAR RECOGNITION; REACTION ANALYSIS;

ANTIVIRAL AGENTS; DISTAMYCINS; DNA; DNA TOPOISOMERASES, TYPE II; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; NYLONS; OLIGOPEPTIDES; PYRROLES; THIAZOLES;

EID: 0034712243     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991571g     Document Type: Article

References (46)

1. (a) Caruthers, M. H. Acc. Chem. Res. 1980, 13, 155.
2. (b) Frederick, C. A.; Grable, J.; Melia, M.; Samudzi, C.; Jen-Jacobson, L.; Wang, B. C.; Greene, P.; Boyere, H. W.; Rosenberg, J. W. Nature 1984, 309, 327.
3. (c) Gurskii, G. V.; Tumanyan, V. G.; Zavedatelev, A. S.; Zhyze, A. L.; Grokhovsky, S. L.; Gottikhi, B. P. In Nucleic Acid-Protein Recognition; Vogel, H. J., Ed.; Academic Press: New York, 1977; p 189.
4. (d) Kime, S. H.; Sussman, J. L.; Church, G. M. In Structure and Conformation of Nucleic Acids and Protein-Nucleic Acid Interactions; Sundaralingam, M., Rao, S. T., Eds.; University Park Press: Baltimore, MD, 1974; p 571.
5. (e) Takeda, Y.; Ohlendorf, D. H.; Anderson, W. F.; Matthews, B. W. Science 1983, 221, 1020.
6. Stephenson, M. L.; Zamecnik, P. C. Natl. Acad. Sci. U.S.A. 1978, 75, 285.
7. Izant, J. G.; Weintraub, H. Cell 1984, 36, 1007.
8. Holt, J. T.; Gopan, T. V.; Moulton, A. D.; Nienhuis, A. W. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 4794.
9. Miller, P. S.; Agris, C. H.; Aurcliani, L.; Blake, K. R.; Murakami, A.; Reddy, M. P.; Spitz, S. A.; Ts'O, P. O. P. Biochimie 1986, 67, 796.
10. Miller, P. S.; Yano, J.; Yano, E.; Carroll, C.; Jayaraman, K.; Ts'O, P. O. P. Biochemistry 1979, 18, 5134.
11. Ts'O, P. O. P.; Miller, P. S.; Greene, J. J. Development of Target-Oriented Anticancer Drugs; Chong, Y. C., Ed.; Raven Press: New York, 1983, p 189.
12. Smith, C. C.; Aurelin, I.; Reddy, L.; Miller, P. S.; Ts'O, P. O. P. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 2787.
13. Cazenave, C.; Loreau, N.; Toulme, J. J.; Helene, C. Biochimie 1986, 68, 1063.
14. Helene, C.; Monteray-Garestier, T.; Saison, T.; Takasugi, M.; Tolume, J. J.; Asseltine, V.; Lancelot, G.; Maurisot, J. C.; Tolume, F.; Thuong, N. T. Biochimie 1985, 57, 77.
15. Toulme, J. J.; Kirsch, H. M.; Lorcan, N.; Thuong, N. T.; Helene, C. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 1227.
16. Moser, H. E.; Dervan, P. B. Science 1987, 238, 645.
17. Kopka, M. L.; Yoon, C.; Goodshell, D.; Pjura, P.; Dickerson, R. E. J. Mol. Biol. 1985, 183, 553.
18. Julia, M.; Preau-Joseph, N. Bull. Soc. Chim. Fr. 1967, 4348.
19. Arcamone, F.; Orezzi, P. G.; Barbieri, W.; Nicollella, V.; Penco, S. Gazz. Chim. Ital. 1967, 97, 1097.
20. Hahn, F. E. In Antibiotics III Mechanism of Action of Antimicrobial and Antitumor Agents; Corcoran, J. W., Hahn, F. E., Eds.; Springer-Verlag: New York, 1975; p 79.
21. Probst, G. W.; Hoehn, M. M.; Woods, B. L. Antimicrob. Agents Chemother. 1965, 789.
22. Takaishi, T.; Sugawara, Y.; Suzuki, M. Tetrahedron Lett. 1972, 1873.
23. Nakamura, S.; Karasawa, K.; Yonehara, H.; Tanaka, N.; Umezawa, H. J. Antibiot. (Tokyo), Ser. A 1961, 14, 103.
24. Diana, G. D. J. Med. Chem. 1973, 16, 857.
25. Godshell, D. S.; Dickerson, R. E. J. Med. Chem. 1986, 29, 727.
26. Lown, J. W.; Krowicki, K.; Bhat, U. G.; Skorobogaty, A.; Dabrowiak, J. C. Biochemistry 1986, 25, 7408.
27. Kissinger, K.; Krowicki, K.; Dabrowiak, J. C.; Lown, J. W. Biochemistry 1987, 26, 5590.
28. Lee, M.; Chang, d. K.; Hartley, J. A.; Pon, R. T.; Krowicki, K.; Lown, J. W. Biochemistry 1988, 27, 445.
29. Lee, M.; Rhodes, A. L.; Wyatt, M. D.; Forro, W. S.; Hartley, J. A. Biochemistry 1993, 32, 4237.
30. Pelton, J. G.; Wemmer, D. E. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 5723.
31. Mrksich, M.; Parks, M. E.; Dervan, P. B. J. Am. Chem. Soc. 1994, 116, 7983.
32. Chen, Y. H.; Lown, J. W. J. Am. Chem. Soc. 1994, 116, 6995.
33. Mrksich, M.; Dervan, P. B. J. Am. Chem. Soc. 1994, 116, 3663.
34. Chipman, D. M.; Sharon, M. Science 1965, 165, 454.
35. Henichart, J. P.; Beuvien, J. L.; Helbecque, N.; Houssin, R. Nucleic Acids Res. 1985, 13, 6703.
36. Kasai, H.; Naganawa, H.; Takita, H.; Umezawa, H. J. Antibiot. (Tokyo) 1978, 32, 1316.
37. Rao, K. E.; Shea, R. G.; Yadagri, B.; Lown, J. W. Anti-Cancer Drug Des. 1990, 5, 3.
38. Kopka, M. L.; Han, G. W.; Goodsell, D. S.; Chiu, T. K.; Walker, W. L.; Lown, J. W.; Dickerson, R. E. In Structure, Motion, Interaction and Expression of Biological Macromolecules; Sarma, R. H., Sarma, M. H., Eds.; Proceedings of the Tenth Conversation, State University New York, Albany, NY; Adenine Press: Guilderland, NY, 1998; p 177.
39. (a) Lown, J. W. Antiviral Res. 1992, 17, 179.
40. (b) Dwyer, T. J.; Geierstanger, B. H.; Yadagri, B.; Lown, J. W. J. Am. Chem. Soc. 1992, 114, 5911.
41. (c) Geierstanger, B. H.; Dwyer, T. J.; Yadagiri, Y.; Lown, J. W.; Wemmer, D. E. J. Am. Chem. Soc. 1993, 115, 4472.
42. Chen, Y. H.; Yang, Y.; Lown, J. W. J. Biomol. Struct. Dyn. 1996, 14, 341.
43. Nishwaki, E.; Tanaka, S.; Lee, H.; Shibuya, M. Heterocycles 1988, 27, 1945.
44. Dodson, R. M.; King, L. C. J. Am. Chem. Soc. 1945, 67, 2242.
45. Braun, J. A.; Metzger, J. Bull. Soc. Chim. Fr. 1967, 2, 503
46. Burchardt, G.; Fortsch, I.; Simon, H.; Hirschfeld, E. B.; Kittler, L.; Schutz, H.; Sharma, S. K.; Lown, J. W.; Zimmer, C. J. Biomol. Struct. Dyn., in press.