The elusive 8-fluoroadenosine: a simple non-enzymatic synthesis and characterization

Tetrahedron

Volumn 63, Issue 18, 2007, Pages 3782-3789

  Butora, Gabor ^a   Schmitt, Christoph ^a   Levorse, Dorothy A ^a   Streckfuss, Eric ^a   Doss, George A ^a   MacCoss, Malcolm ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 FLUOROADENOSINE; ADENOSINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; MOLECULAR STABILITY; PH; PRIORITY JOURNAL; REACTION ANALYSIS; REACTION TIME; SUBSTITUTION REACTION; SYNTHESIS;

EID: 33947643729     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.02.053     Document Type: Article

References (28)

1. Sekine M., Okada K., Seio K., Kakeya H., Osada H., and Sasaki T. Bioorg. Med. Chem. 12 (2004) 5193-5201
2. Van Aerschot A.A., Mamos P., Weyns N.J., Ikeda S., De Clercq E., and Herdewijn P.A. J. Med. Chem. 36 (1993) 2938-2942
3. Holmes R.E., and Robins R.K. J. Am. Chem. Soc. 86 (1964) 1242-1245
4. Chatgilialoglu C., Navacchia M.L., and Postigo A. Tetrahedron Lett. 47 (2006) 711-714
5. Frieden M., Avino A., and Eritja R. Nucleosides Nucleotides Nucleic Acids. 22 (2003) 193-202
6. Kohyama N., Katashima T., and Yamamoto Y. Synthesis 17 (2004) 2799-2804
7. Mamos P., Vanaerschot A.A., Weyns N.J., and Herdewijn P.A. Tetrahedron Lett. 33 (1992) 2413-2416
8. Brentnall H.J., and Hutchinson D.W. Tetrahedron Lett. 13 (1972) 2595-2596
9. Ikehara M., and Yamada K. Chem. Pharm. Bull. (Tokyo) 19 (1971) 104-109
10. Jansons J., Maurinsh Y., and Lidaks M. Nucleosides Nucleotides 14 (1995) 1709-1724
11. Manfredini S., Baraldi P.G., Bazzanini R., Marangoni M., Simoni D., Balzarini J., and De Clercq E. J. Med. Chem. 38 (1995) 199-203
12. Lang P., Gerez C., Tritsch D., Fontecave M., Biellmann J.F., and Burger A. Tetrahedron 59 (2003) 7315-7322
13. Ratsep P.C., Robins R.K., and Vaghefi M.M. Nucleosides Nucleotides 9 (1990) 197-204
14. Barrio J.R., Namavari M., Keen R.E., and Satyamurthy N. Tetrahedron Lett. 39 (1998) 7231-7234
15. Ikehara M., and Kaneko M. Tetrahedron 26 (1970) 4251-4259
16. Prakash T.P., Kumar R.K., and Ganesh K.N. Tetrahedron 49 (1993) 4035-4050
17. Moriarty R.M., Vaid R.K., Hopkins T.E., Vaid B.K., and Prakash O. Tetrahedron Lett. 31 (1990) 201-204
18. Ikehara M., Ogiso Y., and Maruyama T. Chem. Pharm. Bull. (Tokyo) 25 (1977) 575-578
19. Ryu E.K., and MacCoss M. J. Org. Chem. 46 (1981) 2819-2823
20. Ikehara M., and Yamada S. J. Chem. Soc., Chem. Commun. (1968) 1509
21. Kobayashi Y., Kumadaki I., Ohsawa A., and Murakami S. J. Chem. Soc., Chem. Commun. (1976) 430-431
22. Barrio J.R., Namavari M., Phelps M.E., and Satyamurthy N. J. Am. Chem. Soc. 118 (1996) 10408-10411
23. Cristalli G., Costanzi S., Lambertucci C., Lupidi G., Vittori S., Volpini R., and Camaioni E. Med. Res. Rev. 21 (2001) 105-128
24. Sideraki V., Mohamedali K.A., Wilson D.K., Chang Z., Kellems R.E., Quiocho F.A., and Rudolph F.B. Biochemistry 35 (1996) 7862-7872
25. Subrayan R.P., and Rasmussen P.G. Tetrahedron 51 (1995) 6167-6178
26. Ikehara M., Tada H., and Kaneko M. Tetrahedron 24 (1968) 3489-3498
27. Ikehara M., Kaneko M., and Okano R. Tetrahedron 26 (1970) 5675-5682
28. Gundersen L.L. Acta Chem. Scand. 50 (1996) 58-63