A convenient synthesis of 2'-deoxy-2-fluoroadenosine; a potential prodrug for suicide gene therapy

Nucleosides, Nucleotides and Nucleic Acids

Volumn 19, Issue 3, 2000, Pages 559-565

  Hassan, Abdalla E A ^a   Shortnacy Fowler, Anita T ^a   Montgomery, John A ^a   Secrist III, John A ^a  

^a SOUTHERN RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2' DEOXY 2 FLUOROADENOSINE; ADENOSINE DERIVATIVE; PRODRUG; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CELL KILLING; DRUG SYNTHESIS; FLUORINATION; GENE THERAPY; HYDROLYSIS; PROTEIN SYNTHESIS INHIBITION; REACTION ANALYSIS; RNA SYNTHESIS; SIALYLATION; SUICIDE GENE; TUMOR CELL;

EID: 0033995672     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1080/15257770008035007     Document Type: Article

References (22)

1. For reviews on this topic see: a) Moolten, F. L. Cancer Gene Ther., 1994, 4, 279-287.
2. b) Kramm, C. M.; Sena-Esteves, M.; Barnett, F. H.; Rainov, N. G.; Schuback, D. E.; Yu, J.S.; Pechan, P. A.; Paulus, W.; Chiocca, E. A.; Breakefield, X. O. Brain Pathol., 1995, 5, 345-381.
3. c) Anderson, W. F. Science, 1992, 256, 808-813.
4. d) Miller, A. D. Nature, 1992, 357, 455-460.
5. a) Sorscher, E. J.; Peng, S.; Bebok, Z.; Allan, P. W.; Bennett, L. L., Jr.; Parker, W. B. Gene Ther., 1994, 1, 233-238.
6. b) Parker, W. B.; King, S. A.; Allan, P. W.; Bennett, L. L., Jr.; Secrist, J. A., III; Montgomery, J. A.; Gilbert, K. S.; Waud, W. R.; Wells, A. H.; Gillespie, G. Y.; Sorscher, E. J. Hum. Gene Ther., 1997, 8, 1637-1644.
7. c) Waud, W. R.; Gilbert, K. G.; Parker, W. B.; Secrist, J. A., III; Montgomery, J. A.; Bennett, L. L., Jr.; Sorscher, E. J. Proc. Amer. Assoc. Cancer Res., 1998, 39, 512.
8. Montgomery, J. A.; Hewson, K. J. Med. Chem., 1969, 12, 498-504.
9. Parker, W. B.; Allan, P. W.; Shaddix, S. C.; Rose, L. M.; Speegle, H. F.; Gillespie, G. Y.; Bennett, L. L., Jr. Biochem. Pharmacol., 1998, 55, 1673-1681.
10. Huang, M.-C.; Hatfield, K.; Roetker, A. W.; Montgomery, J.A.;. Blakley, R. L. Biochem. Pharmacol, 1981, 30, 2663-2671.
11. Secrist, J. A., III; Shortnacy, A. T.; Montgomery, J. A. J. Med. Chem., 1988, 31, 405-410.
12. a) Krolikiewicz, K.; Vorbruggen, H. Nucleosides Nucleotides, 1994, 13, 673-678.
13. b) Olah, G. A., Welch, J. T., Vankar, Y. D., Nojima, M., Kerekes, I., Olah, J. A. J. Org. Chem. 1979, 44, 3872-3881.
14. a) Barton, D. H. R.; McCombie, S. W. J. Chem. Soc. Chem. Perkin Trans. 1, 1975, 1574-1585.
15. b) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. C. Tetrahedron Lett., 1991, 32, 7187-7190.
16. c) Barton, D. H. R.; Jang, D. O.; Jaszberenyi, J. C. Tetrahedron Lett., 1992, 33, 6629-6632.
17. Chatgilialoglu, C. Acc. Chem. Res., 1992, 25, 188-194.
18. a,b;
19. b) The signal of the H-1′ proton appeared as a doublet of doublets, confirming the 2′-deoxy derivative, which was further confirmed by NOE experiments;
20. 13C-NMR spectra.
21. a) Chen, Y.; Bauman, J. G.; Chu, C. K. Nucleosides Nucleotides, 1992, 11, 693-705, and references cited therein.
22. b) Sakata, S.; Yonei, S.; Yoshino, H. Chem. Pharm. Bull., 1982, 30, 2583-2585.