Synthesis of 4'-C-fluoromethylnucleosides as potential antineoplastic agents

Tetrahedron

Volumn 53, Issue 39, 1997, Pages 13315-13322

  Kitano, Kenji ^a   Miura, Shinji ^a   Ohrui, Hiroshi ^b   Meguro, Hiroshi ^b  

^a YAMASA CORPORATION   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; NUCLEOSIDE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030775459     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00844-2     Document Type: Article

References (23)

1. a) 4′-C-Hydroxymethylnucleosides: Youssefyeh, R. D.; Verheyden, J. P.; Moffatt, J. G. J. Org. Chem., 1979, 44, 1301.
2. b) S-(4′-Methyladenosyl)-L-homocysteine: Johnson, C. R.; Esker, J. L.; Van Zandt, M. C. J. Org. Chem., 1994, 59, 5854.
3. c) 4′-C-Branched 2′,3′-didehydro-2′,3′-dideoxyribonucleosides: Haraguchi, K.; Tanaka, H.; Itoh, Y.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem., 1996, 61, 851.
4. Maag, H.; Rydzewski, R. M.; McRoberts, M. J.; Crawford-Ruth, D; Verheyden, J. P. H.; Prisbe, E. J. J. Med. Chem. 1992, 35, 1440.
5. O-Yang, O.; Wu, H. Y.; Fraser-Smith, E. B.; Walker, K. A. M. Tetrahedron Lett. 1992, 33, 37.
6. Waga, T.; Ohrui, H.; Meguro, H. Nucleosides Nucleotides 1996, 15, 287.
7. Resnati, G. Tetrahedron, 1993, 49, 9385.
8. a) Bergstorm, D. E.; Swartling, D. J. In Fluorine-containing molecules : structure, reactivity, synthesis, and applications; Liebman, J. F.; Greenberg, A.; Dolbier, Jr. W. R. Eds.; VCH Publishers, Inc.: New York, 1988; pp. 259-308.
9. b) Herdewijn, P.; Aerschot, A. V.; Kerremans, L. Nucleosides Nucleotides 1989, 8, 65.
10. a) Hertel, L. W.; Kroin, J. S.; Misner, J. W.; Tustin, J. M. J. Org. Chem. 1988, 53, 2406.
11. b) Hertel, L. W.; Boder, G. B.; Kroin, J. S.; Rinzel, S. M.; Poore, G. A.; Todd, G. C.; Grindey, G. B. Cancer Res. 1990, 50, 4417.
12. c) Braakhuis, B. J. M.; van Dongen, G. A. M. S.; Vermorken, J. B.; Snow, G. B. Cancer Res. 1991, 51, 211.
13. Waga, T; Nishizaki, T; Miyakawa, I; Ohrui, H; Meguro, H. Biosci. Biotech. Biochem. 1993, 57, 1433.
14. a) Middleton, W. J. J. Org. Chem. 1975, 40, 574.
15. b) Hudlicky, M. Org. React. 1988, 35, 513.
16. DAST treatment in dichloromethane at reflux has not been examined.
17. 1-H with that of 4-C-methyl derivative described in ref 8.
18. Robins, M. J.; Wilson, J. S.; Hansske, F. J. Am. Chem. Soc. 1983, 105, 4059.
19. a) Divaker, K. J.; Reese C. B. J. Chem. Soc., Perkin Trans 1, 1982, 1171.
20. b) Lin, T.-S.; Luo, M.-Z.; Liu, M.-C. Tetrahedron, 1995, 51, 1055.
21. Agyei-Aye, K.; Yan, S.; Hebbler, A. K.; Baker, D. C. Nucleosides Nucleotides 1989, 8, 327.
22. a) Mossman, T. J. Immunol. Meth. 1983, 65, 55.
23. b) Hansen, M. B.; Nielsen, S. E.; Berg, K. J. Immunol. Meth. 1989, 119, 203.