Dideoxygenated purine nucleosides substituted at the 8-position: Chemical synthesis and stability

Synthesis (Germany)

Volumn 1990, Issue 10, 1990, Pages 962-966

  Buenger, Greg S ^a   Nair, Vasu ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEOXY 8 HYDROXYADENOSINE; 2',3' DIDEOXY 8 HYDROXYINOSINE; 2',3' DIDEOXYADENOSINE DERIVATIVE; 8 AMINO 2',3' DIDEOXYADENOSINE; 8 AMINO 2',3' DIDEOXYINOSINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0025044033     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-1990-27066     Document Type: Article

References (25)

1. Presented in part at the 198th National Meeting of the American Chemical Society, Miami Beach, Florida, September 10-15, 1989.
2. Mitsuya, H.; Broder, S. Proc. Natl. Acad. Sci. USA 1986, 83, 1911.
3. Mitsuya, H.; Weinhold, K.J.; Furman, P.A.; St. Clair, M.H.; Lehrman, S.N.; Gallo, R.L.; Bolognesi, D.; Barry, D.W.; Broder, S. Proc. Natl. Acad. Sci. USA 1985, 82, 7096.
4. Lin, T.S.; Shen, Z.Y.; August, E.M.; Brankovan, V.; Yang, H.; Ghazzouli, I.; Prusoff, W.H. J. Med. Chem. 1989, 32, 1891.
5. Chu, C.K.; Schinazi, R.F.; Ahn, M.K.; Ullas, G.V.; Gu, Z.P. J. Med. Chem. 1989, 32, 612.
6. Van Aerschot, A.; Herdewijn, P.; Balzarini, J.; Pauwels, R.; De Clercq, E. J. Med. Chem. 1989, 32, 1743.
7. Lin, T.S.; Chen, M.S.; McLaren, C.; Gao, Y.S.; Ghazzouli, I.; Prusoff, W.H. J. Med. Chem. 1987, 30, 440.
8. Balzarini, J.; Pauwels, R.; Baba, M.; Robins, M. J.; Zou, R.; Herdewijn, P.; De Clercq, E. Biochem. Biophys. Res. Commun. 1987, 145, 269.
9. Herdewijn, P.; Balzarini, J.; Baba, M.; Pauwels, R.; Van Aerschot, A.; Janssen, G.; De Clercq, E. J. Med. Chem. 1988, 31, 2040.
10. Haertle, T.; Carrera, C.J.; Wasson, D.B.; Sowers, L.C.; Richman, D.D.; Carson, D.A. J. Biol. Chem. 1988, 263, 5870.
11. Koszalka, G.W.; Krenitsky, T. A.; Rideout, J.L.; Burns, C.L. European Patent Appl. EP 286425
12. C. A. 1989, 111, 23910.
13. Ikahara, M.; Uesugi, S.; Kaneko, M., in: Nucleic Acid Chemistry, Townsend, L. B.; Tipson, R. S.; (eds.), John Wiley & Sons, New York, NY, Vol. 2, 1978, p. 837.
14. Matsuda, A.; Nomoto, Y.; Ueda, T. Chem. Pharm. Bull. 1979, 27, 183.
15. Nair, V.; Buenger, G.S. J. Am. Chem. Soc. 1989, 111, 8502.
16. Barton, D.H.R.; Subramanian, R. J. Chem. Soc., Perkin Trans. 1 1977, 1718.
17. Holmes, R.E.; Robins, R.K. J. Am. Chem. Soc. 1965, 87, 1772.
18. Ogilvie, K.K.; Slotin, L. J. Org. Chem. 1971, 36, 2556.
19. Schmidt, R.; Manolson, M.F.; Angelides, K.J.; Poole, R.J. FEBS Lett. 1981, 129, 305.
20. Scriven, E.F.V.; Turnbull, K. Chem. Rev. 1988, 88, 297.
21. Agarwal, R.P.; Sagar, S.M.; Parks, R.E., Jr. Biochem. Pharmacol. 1975, 24, 693.
22. Wolfenden, R.; Kaufman, J.; Macon, J.B. Biochemistry 1969, 5, 2412.
23. Simon, L.N.; Bauer, R.J.; Tolman, R.T.; Robins, R.K. Biochemistry 1970, 9, 573.
24. Ikehara, M.; Fukui, T. Biochim. Biophys. Acta 1974, 338, 512.
25. Nair, V.; Wiechert, R.J. Bioorg. Chem. 1980, 9, 423.