Definitive solution structures for the 6-formylated versions of 1-(β-D-ribofuranosyl)-, 1-(2′-deoxy-β-D-ribofuranosyl)-, and 1-β-D-arabinofuranosyluracil, and of thymidine

Nucleosides and Nucleotides

Volumn 15, Issue 5, 1996, Pages 1041-1057

  Groziak, Michael P ^a   Lin, Ronghui ^a   Stevens, William C ^a   Wotring, Linda L ^b   Townsend, Leroy B ^b   Balzarini, J ^c   Witvrouw, M ^c   De Clercq, E ^c  

^a SOUTHERN ILLINOIS UNIVERSITY   (United States)

^b UNIVERSITY OF MICHIGAN   (United States)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIMIDINE NUCLEOSIDE; URIDINE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; BREAST CANCER; CANCER INHIBITION; CELL GROWTH; CRYSTALLIZATION; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE; PROTEIN SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 0029936835     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319608002033     Document Type: Article

References (28)

1. (a) Groziak, M. P.; Koohang, A. J. Org. Chem. 1992, 57, 940;
2. (b) Groziak, M. P.; Koohang, A.; Stevens, W. C.; Robinson, P. D. J. Org. Chem. 1993, 58, 4054.
3. (a) Kittaka, A.; Tanaka, H.; Odanaka, Y.; Ohnuki, K.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1994, 59, 3636;
4. (b) Garg, N.; Hossain, N.; Chattopadhyaya, J. Tetrahedron 1994, 50, 5273;
5. (c) Camarasa, M.-J.; Pérez-Pérez, M.-J.; San-Félix, A.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1992, 35, 2721.
6. (a) Hsu, L.-Y.; Wise, D. S.; Drach, J. C.; Townsend, L. B. Chin. Pharm. J. 1991, 43, 275;
7. (b) Hsu, L.-Y.; Wise, D. S.; Kucera, L. S.; Drach, J. C.; Townsend, L. B. J. Org. Chem. 1992, 57, 3354.
8. Otter, B. A.; Patil, S. A.; Spada, M. R.; Micks, L. A.; Yoshimura, Y.; Matsuda, A.; Klein, R. S. Nucleosides Nucleotides 1992, 11, 615. These workers prepared the 2′,3′-O-isopropylidenated 1a and characterized its 7,O5′-hemiacetal solution structure.
9. Kessler, H.; Griesinger, C.; Kerssebaum, R.; Wagner, K.; Ernst, R. R. J. Am. Chem. Soc. 1987, 109, 607.
10. States, D. J.; Haberkorn, R. A.; Ruben, D. J. J. Magn. Res. 1982, 48, 286.
11. Skehan, P. J.; Storeng, R.; Scudiero, D. A.; Monks, A.; McMahon, J. B.; Vistica, D. T.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. J. Natl. Cancer Inst. 1990, 82, 1107.
12. Tanaka, H.; Hayakawa, H.; Shibata, S.; Haraguchi, K.; Miyasaka, T. Nucleosides Nucleotides 1992, 11, 319.
13. Schinazi, R. F.; Chen, M. S.; Prusoff, W. H. J. Med. Chem. 1979, 22, 1273.
14. Ogilvie, K. K. Can. J. Chem. 1973, 51, 3799.
15. Zee-Cheng, K.-Y.; Cheng, C. C. J. Heterocycl. Chem. 1967, 4, 163.
16. Ti, G. S.; Gaffney, B. L.; Jones, R. A. J. Am. Chem. Soc. 1982, 104, 1316.
17. (a) Pichat, L.; Godbillon, J.; Herbert, M. Bull. Soc. Chim. Fr. 1973, 2715;
18. (b) Pichat, L.; Godbillon, J.; Herbert, M. Bull. Soc. Chim. Fr. 1973, 2709.
19. (a) Tanaka, H.; Nasu, I.; Miyasaka, T. Tetrahedron Lett. 1979, 4755;
20. (b) Tanaka, H.; Hayakawa, H.; Miyasaka, T. Chem. Pharm. Bull. 1981, 29, 3565;
21. (c) Tanaka, H.; Hayakawa, H.; Miyasaka, T. Tetrahedron 1982, 38, 2635;
22. (d) Tanaka, H.; Hayakawa, H.; Iijima, S.; Haraguchi, K.; Miyasaka, T. Tetrahedron 1985, 41, 861.
23. Fessenden, R.; Crowe, D. F. J. Org. Chem. 1961, 26, 4638.
24. Ikehira, H.; Matsuura, T.; Saito, I. Tetrahedron Lett. 1984, 25, 3325.
25. Megati, S.; Sodum, R.; Otter, G. M.; Klein, R. S.; Otter, B. A. Bioorg. Med. Chem. Lett. 1994, 4, 469.
26. Hayakawa, H.; Tanaka, H.; Maruyama, Y.; Miyasaka, T. Chem. Lett. 1985, 1401.
27. Neuhaus, D.; Williamson, M. "The Nuclear Overhauser Effect in Structural and Conformational Analysis", VCH Publishers: 1989, New York, p. 318.
28. Megati, S.; Ealick, S. E.; Naguib, R. N. M.; el Kouni, M. H.; Klein, R. S.; Otter, B. A. Nucleosides Nucleotides 1994, 13, 2151.