Synthesis and anti-HIV activity of L-2'-fluoro-2',3'-unsaturated purine nucleosides

Tetrahedron Letters

Volumn 39, Issue 25, 1998, Pages 4437-4440

  Choi, Yongseok ^a   Lee, Kyeong ^a   Hong, Joon H ^a   Schinazi, Raymond F ^b   Chu, Chung K ^a  

^a UNIVERSITY OF GEORGIA   (United States)

^b EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2',3' DIDEOXY 2' FLUOROADENOSINE; 9 (2,3 DIDEOXY 2 FLUORO GLYCERO PENT 2 ENO FURANOSYL)ADENINE; 9 (2,3 DIDEOXY 2 FLUORO GLYCERO PENT 2 ENO FURANOSYL)HYPOXANTHINE; ADENINE NUCLEOTIDE DERIVATIVE; HYPOXANTHINE DERIVATIVE; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; LYMPHOCYTE; NONHUMAN; NUCLEOTIDE METABOLISM; VERO CELL;

ANIMALIA; HUMAN IMMUNODEFICIENCY VIRUS; HUMAN IMMUNODEFICIENCY VIRUS 1;

EID: 0032543455     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00841-7     Document Type: Article

References (27)

1. 1. Furman, P. A.; Fyfe, J. A.; St. Clair, M. H.; Weinhold, K.; Rideout, J. L.; Freeman, G. A.; Nusinoff-Lehrman, S.; Bolognesi, D. P.; Broder, S.; Mitsuya, H.; Barry, D. W. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 8333-8337.
2. 2. Yarchoan, R.; Thomas, R. V.; Allain, J.-P.; McAtee, N.; Dubinsky, R.; Mitsuya, H.; Lawley, T. J.; Safai, B.; Myers, C. E.; Perno, C. F.; Klecker, R. W.; Wills, R. J.; Fischl, M. A.; McNeely, M. C.; Pluda, J. M.; Leuther, M.; Collins, J. M.; Broder, S. Lancet 1988, 1, 76-80.
3. 3. Yarchoan, R.; Mitsuya, H.; Thomas, R. V.; Pluda, J. M.; Hartman, N. R.; Perno, C. F.; Marczyk, K. S.; Allain, J. P.; Johns, D. G.; Broder, S. Science 1989, 245, 412-415.
4. 4. Lin, T.-S.; Schinazi, R. F.; Prusoff, W. H. Biochem. Pharmacol. 1987, 36, 2713-2718.
5. 5. (a) Coates, J. A. V.; Cammack, N.; Jenkinson, H. J.; Mutton, I. M.; Pearson, B.A.; Storer, R.; Cameron, J. M.; Penn, C. R. Antimicrob. Agents Chemother. 1992, 36, 202-205.
6. (b) Schinazi, R. F.; Chu, C. K.; Peck, A.; McMillan, A.; Mathis, R.; Cannon, D.; Jeong, L. S.; Beach, J. W.; Choi, W. B.; Yeola, S.; Liotta, D. C. Antimicrob. Agents Chemother. 1992, 36, 672-676.
7. 6. Schinazi, R. F.; McMillan, A.; Cannon, D.; Mathis, R.; Lloyd, R. M.; Peck, A.; Sommadossi, J.-P.; St. Clair, M.; Wilson, J.; Furman, P. A.; Painter, G.; Choi, W. B.; Liotta, D. C. Antimicrob. Agents Chemother. 1992, 36, 2423-2431.
8. 7. Chu, C. K.; Ma, T. W.; Shanmuganathan, K.; Wang, C. G.; Xiang, Y. J.; Pai, S. B.; Yao, G. Q.; Sommadossi, J.-P.; Cheng, Y.-C. Antimicrob. Agents Chemother. 1995, 39, 979-981.
9. 8. Bolon, P. J.; Wang, P. Y.; Chu, C. K.; Gosselin, G.; Boudou, V.; Pierra, C.; Mathe, C.; Imbach, J.-L.; Faraj, A.; Alaoui, M. A.; Sommadossi, J.-P.; Pai, S. B.; Zhu, Y.-L.; Lin, J.-S.; Cheng, Y.-C.; Schinazi, R. F. Bioorg. & Med. Chem. Lett. 1996, 6, 1657-1662.
10. 9. (a) Garrett, E. R.; Mehta, P. J. J. Am. Chem. Soc. 1972, 94, 8532-8541.
11. (b) York, J. L. J. Org. Chem. 1981, 46, 2171-2173.
12. (c) Russel, J. W.; Klunk, L. J. Biochem. Pharmacol. 1989, 38, 1385-1388.
13. 10. (a) Marquez, V. E.; Tseng, C. K.-H.; Mitsuya, H.; Aoki, S.; Kelley, J. A.; Ford, Jr., H.; Roth, J. S.; Broder, S.; Johns, D. G.; Driscoll, J. S. J. Med. Chem. 1990, 33, 978-985.
14. (b) Ruxrungtham, K.; Boone, E.; Ford, Jr., H.; Driscoll, J. S.; Davey, R. T.; Lane, H. C. Antimicrob. Agents Chemother. 1996, 40, 2369-2374.
15. 11. (a) Watanabe, K. A.; Su, T.-L.; Lein, R. S.; Chu, C. K.; Matsuda, A.; Chun, M. W.; Lopez, C.; Fox, J. J. J. Med. Chem. 1983, 26, 152-156.
16. (b) Ma, T. W.; Pai, S. B.; Zhu, Y. L.; Lin, J. S.; Shamuganathan, K.; Du, J. F.; Wang, C.; Kim, H. B.; Newton, M. G.; Cheng, Y.-C.; Chu, C. K. J. Med. Chem. 1996, 39, 2835-2843.
17. 12. (a) Martin, J. A.; Bushnell, D. J.; Duncan, I. B.; Dunsdon, S. J.; Hall, M. J.; Machin, P. J.; Merret, J. H.; Parkes, K. E. B.; Roberts, N. A.; Thomas, G. J.; Galpin, S. A.; Kinchington, D. J. Med. Chem. 1990, 33, 2137-2145.
18. (b) Stezycki, R. Z.; Ghazzouli, I.; Brankovan, V.; Martin, J. C.; Mansuri, M. M. J. Med. Chem. 1990, 33, 2150-2157.
19. 13. (a) Abdel-Megied, A. E.-S.; Pedersen, E. B.; Nielsen, C. M. Synthesis 1991, 313-317.
20. (b) Sujino, K.; Yoshida, T.; Sugimura, H. Tetrahedron Lett. 1996, 37, 6133-6136.
21. 14. (a) Thenappan, A.; Burton, D. J. J. Org. Chem. 1990, 55, 4639-4642.
22. (b) Morikawa, T.; Sasaki, H.; Mori, K.; Shiro, M.; Taguchi, T. Chem. Pharm. Bull. 1992, 40, 3189-3193.
23. (c) Patrick, T. B.; Lanahan, M. V.; Yang, C.; Walker, J. K.; Hutchinson, C. L.; Neal, B. E. J. Org. Chem. 1994, 59, 1210-1212.
24. 2O: C, 47.13; H, 4.11; N, 27.48. Found: C, 47.02; H, 4.13; N, 27.26.
25. 2·0.3MeOH: C, 47.33; H, 4.33; N, 26.85. Found: C, 47.42; H, 4.23; N, 26.91.
26. 3·0.2MeOH: C, 47.37; H, 3.82; N, 21.66. Found: C, 47.11; H, 3.77; N, 21.50.
27. 2O: C, 46.62; H, 3.76; N, 21.75. Found: C, 46.86; H, 3.80; N, 21.56.