Synthesis and antiviral activity of acyclic analogues of 1,5-anhydrohexitol nucleosides using Mitsunobu reaction

Tetrahedron

Volumn 52, Issue 43, 1996, Pages 13655-13670

  Hossain, Nafizal ^a   Rozenski, Jef ^a   De Clercq, Erik ^a   Herdewijn, Piet ^a  

^a REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; NUCLEOSIDE DERIVATIVE;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

ANIMALIA;

EID: 0030597014     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00818-6     Document Type: Article

References (24)

1. 1. Schaeffer, H. J; Beauchamp, L.; de Miranda, P.; Elion, G. B.; Bauer, D. J.; Collins, P. Nature 1978, 272, 583-585.
2. 2. Chu, C. K.; Culter, S. J. J. Heterocycl. Chem. 1986, 23, 289-319.
3. 3. (a) De Clercq, E.; Descamps, J.; De Somer, P.; Holy, A. Science 1978, 200, 563-565.
4. (b) Martin, J. C.; Dvorak, C. A.; Smee, D. F.; Matthews, T. R.; Verheyden, J. P. H. J. Med. Chem. 1983, 26, 759-761.
5. (c) Smith, K. O.; Galloway, K. S.; Kenell, W. L.; Ogilvie, K. K.; Radatus, B. K. Antimicrob. Agents Chemother. 1982, 22, 55-61.
6. (d) Field, A. K.; Davies, M. E.; DeWitt, C.; Perry, H. C.; Liou, R.; Germershausen, J.; Karkas, J. D.; Ashton, W. T.; Johnston, D. B. R.; Tolman, R. L. Proc. Natl. Acad. Sci. U.S.A. 1983, 80, 4139-4143.
7. (e) Ashton, W. T.; Canning, L. F.; Reynolds, G. F.; Tolman, R. L.; Karkas, J. D.; Liou, R.; Davies, M-E. M.; DeWitt, C. M.; Perry, H. C.; Field, A. K. J. Med. Chem. 1985, 28, 926-933.
8. (f) Larsson, A.; Oberg, B.; Alenius, S.; Hagberg, C.-E.; Johnsson, N.-G.; Lindborg, B., Stenning, G. Antimicrob. Agents Chemother. 1983, 23, 644-670.
9. (g) Harnden, M. R.; Wyatt, P. G.; Boyd, M. R.; Sutton, D. J. Med. Chem. 1990, 33, 187-196.
10. (h) Bailey, S.; Harnden, M. R.; Jarvest, R. L.; Parkin, A.; Boyd, M. R. J. Med. Chem. 1991, 34, 57-65.
11. (i) Vandendriessche, F.; Snoeck, R.; Janssen, G.; Hoogmartens, J.; Van Aerschot, A.; De Clercq, E.; Herdewijn, P. J. Med. Chem. 1992, 35, 1458-1465.
12. 4. (a) Verheggen, I.; Van Aerschot, A.; Toppet, S.; Snoeck, R.; Janssen, G.; Balzarini, J.; De Clercq, E.; Herdewijn, P. J. Med. Chem. 1993, 36, 2033-2040.
13. (b) Verheggen, I.; Van Aerschot, A.; Van Meervelt, L.; Rozenski, J.; Wiebe, L.; Snoeck, R.; Andrei, G.; Balzarini, J.; Claes, P.; De Clercq, E.; Herdewijn, P. J. Med. Chem. 1995, 38, 826-835.
14. 5. Van Aerschot, A.; Zhigang, N.; Rozenski, J.; Claes, P.; De Clercq, E.; Herdewijn, P. Nucleosides & Nucleotides 1994, 8, 1791-1800.
15. 6. Van Draanen, N.A.; Koszalka, G.W; Nucleosides & Nucleotides 1994, 13, 1679-1693.
16. 7. Hossain, N.; Blaton, N.; Peeters, O.; Rozenski, J.; Herdewijn, P. Tetrahedron 1996 52, 5563-5578.
17. 8. Cocu, F. G.; Posternak, T. Helv. Chim. Acta 1972, 55, 2828-2837.
18. 9. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768-2771.
19. 10. Mitsunobu, O. Synthesis, 1981, 1-28.
20. 11. Pérez-Pérez, M.-J.; Rozenski, J.; Busson, R.; Herdewijn, P. J. Org. Chem. 1995, 60, 1531-1537.
21. 12. Cruickshank, K. A.; Jiricny, J. Reese, C. B. Tetrahedron Lett. 1984, 25, 681-684.
22. 13. Divakar, K. J.; Reese, C. B. J. Chem. Soc. Perkin Trans. 1 1982, 1171-1176.
23. 14. Tippie, M. A.; Martin, J. C.; Smee, D. F.; Matthews, T. R.; Verheyden, J. P. H. Nucleosides & Nucleotides 1984, 3, 525-535.
24. 15. Jindrich, J.; Holy, A.; Dvorakova, H. Collect. Czech. Chem. Commun. 1993, 58, 1645-1667.