Regioselective fluorination of substituted guanines with dilute F2: A facile entry to 8-fluoroguanine derivatives

Journal of Organic Chemistry

Volumn 61, Issue 18, 1996, Pages 6084-6085

  Barrio, Jorge R ^b   Namavari, Mohammad ^b   Phelps, Michael E ^b   Satyamurthy, Nagichettiar ^b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

8 FLUORO 9 [(2 HYDROXYETHOXY)METHYL]GUANINE; 8 FLUOROGUANINE DERIVATIVE; ACICLOVIR; GUANINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME SPECIFICITY; FLUORINATION; HERPES SIMPLEX VIRUS; HUMAN; MELANOMA CELL; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029833494     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960761d     Document Type: Article

References (31)

1. Beaman, A. G.; Robins, R. K. J. Org. Chem. 1963, 28, 2310.
2. Naik, S. R.; Witkowski, J. T.; Robins, R. K. J. Org. Chem. 1973, 38, 4353.
3. Ikehara, M.; Yamada, S. Chem. Pharm. Bull. 1971, 19, 104.
4. Kobayashi, Y.; Kumadaki, I.; Ohsawa, A.; Murakami, S. J. Chem. Soc., Chem. Commun. 1976, 430.
5. Ratsep, P. C.; Robins, R. K.; Vaghefi, M. M. Nucleosides Nucleotides 1990, 9, 197.
6. Sono, M.; Toyoda, N.; Shizuri, Y.; Tori, M. Tetrahedron Lett. 1994, 35, 9237.
7. Walsh, C. In Advances in Enzymology; Meister, A., Ed.; John Wiley & Sons: New York, 1983; Vol. 55, p 197.
8. (a) Welch, J. T. Tetrahedron 1987, 43, 3123.
9. (b) Montgomery, J. A.; Shortnacy, A. T.; Secrist, J. A., III. J. Med. Chem. 1983, 26, 1483.
10. (c) Secrist, J. A., III; Shortnacy, A. T.; Montgomery, J. A. J. Med Chem. 1985, 28, 1740.
11. (d) Secrist, J. A., III; Bennett, L. L., Jr.; Allan, P. W.; Rose, L. M.; Chang, C. H.; Montgomery, J. A. J. Med. Chem. 1986, 29, 2069.
12. (e) Secrist, J. A., III; Shortnacy, A. T.; Montgomery, J. A. J. Med. Chem. 1988, 31, 405.
13. See, for example: Marquez, V. E.; Tseng, C. K.-H.; Mitsuya, H.; Aoki, S.; Kelley, J. A.; Ford, H., Jr.; Roth, J. S.; Broder, S.; Johns, D. G.; Driscoll, J. S. J. Med. Chem. 1990, 33, 978.
14. Rozen, S. Acc. Chem. Res. 1988, 21, 307.
15. Gerstenberger, M. R. C.; Haas, A. Angew. Chem., Int. Ed. Engl. 1981, 20, 647.
16. Lister, J. H., Ed. Purines. In Fused Pyrimidines; Brown, D. J., Ed.; Wiley-Interscience: New York, 1971; Part II, Chapter V, p 135.
17. Fluorine is a highly toxic and reactive gas. However, it can be handled safely by following procedures specifically developed (Braker, W.; Mossman, A. L. Matheson Gas Data Book; Matheson: East Rutherford, NJ, 1971; p 261).
18. (a) Reese, C. B.; Saffhill, R. J. Chem. Soc., Perkin Trans. 1 1972, 2937.
19. (b) Gosselin, G.; Bergogne, M.-C.; De Rudder, J.; De Clercq, E.; Imbach, J.-L. J. Med. Chem. 1987, 30, 982.
20. Matsumoto, H.; Kaneko, C.; Yamada, K.; Takeuchi, T.; Mori, T.; Mizuno, Y. Chem. Pharm. Bull. 1988, 36, 1153.
21. Gosselin, G.; Bergogne, M.-C.; Imbach, J.-L. J. Heterocycl. Chem. 1993, 30, 1229.
22. Barrio, J. R.; Bryant, J. D.; Keyser, G. E. J. Med. Chem. 1980, 23, 572.
23. 19F NMR and high-resolution mass spectra.
24. Lacan, G.; Satyamurthy, N.; Barrio, J. R. J. Org. Chem. 1995, 60, 227.
25. Coenen, H. H.; Moerlein, S. M. J. Fluorine Chem. 1993, 36, 63.
26. Satyamurthy, N.; Namavari, N.; Barrio, J. R. CHEMTECH 1994, 24, 25.
27. Rozen, S.; Gal, C. J. Org. Chem. 1987, 52, 2769.
28. Pross, A. Adv. Phys. Org. Chem. 1985, 21, 99.
29. Ikehara, M.; Fukui, T. Biochim. Biophys. Acta 1974, 338, 512. Orozco, M.; Lluis, C.; Mallol, J.; Canela, E. I.; Franco, R. J. Pharm. Sci. 1990, 79, 133.
30. Ikehara, M.; Fukui, T. Biochim. Biophys. Acta 1974, 338, 512. Orozco, M.; Lluis, C.; Mallol, J.; Canela, E. I.; Franco, R. J. Pharm. Sci. 1990, 79, 133.
31. Srinivasan, A.; Gambhir, S.; Barrio, J. R.; Wu, L.; Namavari, M.; Satyamurthy, N.; Sharfstein, S.; Cherry, S.; Green, A.; Berk, A.; Phelps, M. E.; Herschman, H. R. 1996, submitted.