1,N6-Etheno-7-deaza-2,8-diazaadenosine: Syntheses, properties and conversion to 7-deaza-2,8-diazaadenosine

Organic and Biomolecular Chemistry

Volumn 3, Issue 9, 2005, Pages 1714-1718

  Lin, Wenqing ^a,b   Li, Hong ^a,b   Ming, Xin ^a,b   Seela, Frank ^a,b  

^a UNIVERSITY OF OSNABRÜCK   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; CRYSTALLIZATION; FLUORESCENCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PURIFICATION; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL);

AMMONOLYSIS; CONGENERS; ETHENO NUCLEOSIDES; GLYCOSYLATION;

AROMATIC COMPOUNDS;

STAPHYLOCOCCUS PHAGE 3A;

1,N6 ETHENO 7 DEAZA 2,8 DIAZAADENOSINE; 1,N6-ETHENO-7-DEAZA-2,8-DIAZAADENOSINE; 7 DEAZA 2,8 DIAZAADENOSINE; 7-DEAZA-2,8-DIAZAADENOSINE; ADENOSINE; DRUG DERIVATIVE; HETEROCYCLIC COMPOUND;

ARTICLE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECTROFLUOROMETRY; SYNTHESIS; ULTRAVIOLET SPECTROPHOTOMETRY;

ADENOSINE; AZA COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 18844450243     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b418849g     Document Type: Article

References (38)

1. (a) J. A. Secrist, III, J. R. Barrio, N. J. Leonard and G. Weber, Biochemistry, 1972, 11, 3499-3506;
2. (b) S. C. Srivastava, S. K. Raza and R. Misra, Nucleic Acids Res., 1994, 22, 1296-1304;
3. (c) W. Zhang, R. Rieger, C. Iden and F. Johnson, Chem. Res. Toxicol., 1995, 8, 148-156.
4. G. A. Leonard, K. E. McAuley-Hecht, N. J. Gibson, T. Brown, W. P. Watson and W. N. Hunter, Biochemistry, 1994, 33, 4755-4761.
5. A. K. Basu, M. L. Wood, L. J. Niedernhofer, L. A. Ramos and J. M. Essigmann, Biochemistry, 1993, 32, 12793-12801.
6. F. Seela, H. Rosemeyer, E. Schweinberger and E.-M. Becker, 2005, in preparation.
7. (a) K.-F. Yip and K.-C. Tsou, Tetrahedron Lett., 1973, 33, 3087-3090;
8. (b) K.-C. Tsou, K.-F. Yip, E. E. Miller and K. W. Lo, Nucleic Acids Res., 1974, 1, 1800;
9. (c) T. Sugiyama, E. Schweinberger, Z. Kazimierczuk, N. Ramzaeva, H. Rosemeyer and F. Seela, Chem. Eur. J., 2000, 6, 369-378.
10. H. Paulsen and W. Wintermeyer, Eur. J. Biochem., 1984, 138, 117-123.
11. K.-F. Yip and K.-C. Tsou, J. Org. Chem., 1975, 40, 1066-1070.
12. F. Seela, M. Lindner, V. Glaçon and W. Lin, J. Org. Chem., 2004, 69, 4695-4700.
13. J. A. Montgomery and H. J. Thomas, J. Med. Chem., 1972, 15, 182-187.
14. (a) J. Davoll and K. A. Kerridge, J. Chem. Soc., 1961, 2589-2591;
15. (b) J. A. Montgomery, S. J. Clayton and W. E. Fitzgibbon, Jr., J. Heterocycl. Chem., 1964, 1, 215-216;
16. (c) G. R. Revankar and L. B. Townsend, J. Chem. Soc., Perkin Trans. 1, 1971, 2440-2442;
17. (d) I. A. Korbukh, N. G. Yakunina and M. N. Preobrazhenskaya, Bioorg. Khim., 1980, 6, 1632-1638.
18. R. K. Robins, J. Am. Chem. Soc., 1956, 78, 784-790.
19. (a) G. A. Bhat, J.-L. G. Montero, R. P. Panzica, L. L. Wotring and L. B. Townsend, J. Med. Chem., 1981, 24, 1165-1172;
20. (b) H. B. Cottam, G. R. Revankar and R. K. Robins, Nucleic Acids Res., 1983, 11, 871-882;
21. (c) J. D. Anderson, H. B. Cottam, S. B. Larson, L. D. Nord, G. R. Revankar and R. K. Robins, J. Heterocycl. Chem., 1990, 27, 439-453;
22. (d) J. D. Anderson, N. K. Dalley, G. R. Revankar and R. K. Robins, J. Heterocycl. Chem., 1986, 23, 1869-1878;
23. (e) B. G. Ugarkar, H. B. Cottam, P. A. McKernan, R. K. Robins and G. R. Revankar, J. Med. Chem., 1984, 27, 1026-1030;
24. (f) H. B. Cottam, C. R. Petrie, P. A. McKernan, R. J. Goebel, N. K. Dalley, R. B. Davidson, R. K. Robins and G. R. Revankar, J. Med. Chem., 1984, 27, 1119-1127.
25. F. Seela and H. Steker, Helv. Chim. Acta, 1985, 68, 563-570.
26. G. A. Bhat and L. B. Townsend, J. Chem. Soc., Perkin Trans. 1, 1981, 2387-2392.
27. (a) N. Yamaji and M. Kato, Chem. Lett., 1975, 311-314;
28. (b) N. Yamaji, K. Suda, Y. Onoue and M. Kato, Chem. Pharm. Bull., 1977, 25, 3239-3246.
29. M. Sako, T. Hayashi, K. Hirota and Y. Maki, Chem. Pharm. Bull., 1992, 40, 1656-1658.
30. (a) W. Lin, F. Seela, H. Eickmeier and H. Reuter, Acta Crystallogr., Sect. C, 2004, 60, 566-568;
31. (b) W. Lin, X. Ming, H. Eickmeier and F. Seela, Acta Crystallogr., 2005, in preparation.
32. S. Sprang, R. Scheller, D. Rohrer and M. Sundaralingam, J. Am. Chem. Soc., 1978, 100, 2867-2872.
33. L. van Wijk, C. A. G. Haasnoot, F. A. A. M. de Leeuw, B. D. Huckriede, A. J. A. Westra Hoekzema and C. Altona, PSEUROT 6.3, Leiden Institute of Chemistry, Leiden University, The Netherlands, 1999.
34. E. Westhof, O. Röder, I. Croneiss and H.-D. Lüdemann, Z. Naturforsch., C: Biosci., 1975, 30, 131-140.
35. W. Lin and F. Seela, 2005 submitted.
36. M. Zulauf, PhD Thesis, University of Osnabrück, 1999.
37. R. A. Verapoldi and K. D. Mielenz, A fluorescence standard reference material: quinine sulfate dihydrate, NBS special publication SP 260-64, National Bereau of Standards, Washington DC, 1980, p. 139.
38. D. Onidas, D. Markovitsi, S. Marguet, A. Sharonov and T. Gustavsson, J. Phys. Chem. B, 2002, 106, 11367-11374.