Synthesis of dihydroisoxazole nucleoside and nucleotide analogs

Journal of Organic Chemistry

Volumn 62, Issue 1, 1997, Pages 88-92

  Gi, Hung Jang ^a   Xiang, Yuejun ^a   Schinazi, Raymond F ^b,c   Zhao, Kang ^a  

^a NEW YORK UNIVERSITY   (United States)

^b ATLANTA VA MEDICAL CENTER   (United States)

^c EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ISOXAZOLE DERIVATIVE; NUCLEOSIDE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0031033894     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961779r     Document Type: Article

References (30)

1. Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1475.
2. (a) De Clercq, E. AIDS Res. Human Retrovir. 1992, 8, 119.
3. (b) De Clercq, E. Nucleosides Nucleotides 1994, 13, 1271.
4. For selected recent reviews, see: (a) De Clercq, E. J. Med. Chem. 1995, 38, 2491. (b) Nair, V.; Jahnke, T. S. Antimicrob. Agents Chemother. 1995, 39, 1017. (c) de Clercq, E. Ann. New York Acad. Sci. 1994, 438.
5. For selected recent reviews, see: (a) De Clercq, E. J. Med. Chem. 1995, 38, 2491. (b) Nair, V.; Jahnke, T. S. Antimicrob. Agents Chemother. 1995, 39, 1017. (c) de Clercq, E. Ann. New York Acad. Sci. 1994, 438.
6. For selected recent reviews, see: (a) De Clercq, E. J. Med. Chem. 1995, 38, 2491. (b) Nair, V.; Jahnke, T. S. Antimicrob. Agents Chemother. 1995, 39, 1017. (c) de Clercq, E. Ann. New York Acad. Sci. 1994, 438.
7. For selected recent references, see: (a) Wilson, L. J.; Choi, W.B.; Spurling, T.; Liotta, D. C.; Schinazi, R. F.; Cannon, D.; Painter, G. R.; St. Clair, M.; Furman, P. A. Bioorg. Med. Chem. Lett. 1993, 3, 169. (b) Kim, H. O.; Schinazi, R. F.; Shanmuganathan, K.; Jeong, L. S.; Beach, J. W.; Nampalli, S.; Cannon, D. L.; Chu, C. K. J. Med. Chem. 1993, 36, 519. (c) Schinazi, R. F.; Gosselin, G.; Faraj, A.; Korba, B. E.; Liotta, D. C.; Chu, C. K.; Mathé, C.; Imbach, J.-L.; Sommadossi, J.-P. Antimicrob. Agents Chemother. 1994, 38, 2172. (d) Jin, H.; Siddigui, M. A.; Evans, C. A.; Tse, H. L. A.; Mansour, T. S. J. Org. Chem. 1995, 60, 2621. (e) Liang, C.; Lee, D. W.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 1546 and references therein.
8. For selected recent references, see: (a) Wilson, L. J.; Choi, W.B.; Spurling, T.; Liotta, D. C.; Schinazi, R. F.; Cannon, D.; Painter, G. R.; St. Clair, M.; Furman, P. A. Bioorg. Med. Chem. Lett. 1993, 3, 169. (b) Kim, H. O.; Schinazi, R. F.; Shanmuganathan, K.; Jeong, L. S.; Beach, J. W.; Nampalli, S.; Cannon, D. L.; Chu, C. K. J. Med. Chem. 1993, 36, 519. (c) Schinazi, R. F.; Gosselin, G.; Faraj, A.; Korba, B. E.; Liotta, D. C.; Chu, C. K.; Mathé, C.; Imbach, J.-L.; Sommadossi, J.-P. Antimicrob. Agents Chemother. 1994, 38, 2172. (d) Jin, H.; Siddigui, M. A.; Evans, C. A.; Tse, H. L. A.; Mansour, T. S. J. Org. Chem. 1995, 60, 2621. (e) Liang, C.; Lee, D. W.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 1546 and references therein.
9. For selected recent references, see: (a) Wilson, L. J.; Choi, W.B.; Spurling, T.; Liotta, D. C.; Schinazi, R. F.; Cannon, D.; Painter, G. R.; St. Clair, M.; Furman, P. A. Bioorg. Med. Chem. Lett. 1993, 3, 169. (b) Kim, H. O.; Schinazi, R. F.; Shanmuganathan, K.; Jeong, L. S.; Beach, J. W.; Nampalli, S.; Cannon, D. L.; Chu, C. K. J. Med. Chem. 1993, 36, 519. (c) Schinazi, R. F.; Gosselin, G.; Faraj, A.; Korba, B. E.; Liotta, D. C.; Chu, C. K.; Mathé, C.; Imbach, J.-L.; Sommadossi, J.-P. Antimicrob. Agents Chemother. 1994, 38, 2172. (d) Jin, H.; Siddigui, M. A.; Evans, C. A.; Tse, H. L. A.; Mansour, T. S. J. Org. Chem. 1995, 60, 2621. (e) Liang, C.; Lee, D. W.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 1546 and references therein.
10. For selected recent references, see: (a) Wilson, L. J.; Choi, W.B.; Spurling, T.; Liotta, D. C.; Schinazi, R. F.; Cannon, D.; Painter, G. R.; St. Clair, M.; Furman, P. A. Bioorg. Med. Chem. Lett. 1993, 3, 169. (b) Kim, H. O.; Schinazi, R. F.; Shanmuganathan, K.; Jeong, L. S.; Beach, J. W.; Nampalli, S.; Cannon, D. L.; Chu, C. K. J. Med. Chem. 1993, 36, 519. (c) Schinazi, R. F.; Gosselin, G.; Faraj, A.; Korba, B. E.; Liotta, D. C.; Chu, C. K.; Mathé, C.; Imbach, J.-L.; Sommadossi, J.-P. Antimicrob. Agents Chemother. 1994, 38, 2172. (d) Jin, H.; Siddigui, M. A.; Evans, C. A.; Tse, H. L. A.; Mansour, T. S. J. Org. Chem. 1995, 60, 2621. (e) Liang, C.; Lee, D. W.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 1546 and references therein.
11. For selected recent references, see: (a) Wilson, L. J.; Choi, W.B.; Spurling, T.; Liotta, D. C.; Schinazi, R. F.; Cannon, D.; Painter, G. R.; St. Clair, M.; Furman, P. A. Bioorg. Med. Chem. Lett. 1993, 3, 169. (b) Kim, H. O.; Schinazi, R. F.; Shanmuganathan, K.; Jeong, L. S.; Beach, J. W.; Nampalli, S.; Cannon, D. L.; Chu, C. K. J. Med. Chem. 1993, 36, 519. (c) Schinazi, R. F.; Gosselin, G.; Faraj, A.; Korba, B. E.; Liotta, D. C.; Chu, C. K.; Mathé, C.; Imbach, J.-L.; Sommadossi, J.-P. Antimicrob. Agents Chemother. 1994, 38, 2172. (d) Jin, H.; Siddigui, M. A.; Evans, C. A.; Tse, H. L. A.; Mansour, T. S. J. Org. Chem. 1995, 60, 2621. (e) Liang, C.; Lee, D. W.; Newton, M. G.; Chu, C. K. J. Org. Chem. 1995, 60, 1546 and references therein.
12. Tronchet, J. M. J.; Zsély, M.; Sultan, N. Nucleosides Nucleotides 1994, 13, 2071 and references therein.
13. Sun, L.; Li, P.; Landry D. W.; Zhao, K. Tetrahedron Lett, 1996, 37, 1547.
14. (a) Xiang, Y.; Chen, J.; Schinazi, R. F.; Zhao, K. Tetrahedron Lett. 1995, 36, 7193.
15. (b) Xiang, Y.; Gong, Y.; Zhao, K. Tetrahedron Lett. 1996, 37, 4877.
16. (c) Xiang, Y.; Schinazi, R. F.; Zhao, K. Bioorg. Med. Chem. Lett., in press.
17. Xiang, Y.; Chen, J.; Schinazi, R. F.; Zhao, K. Bioorg. Med. Chem. Lett. 1996, 6, 1051.
18. For selected reviews, see: (a) Kozikowski, A. P. Acc. Chem Res. 1984, 17, 410, (b) Caramella, P.; Grünanger, P. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: Chichester, 1984; Vol. 1, p 291. (c) Curran, D. P. Adv. Cycloaddition 1988, 1, 129.
19. For selected reviews, see: (a) Kozikowski, A. P. Acc. Chem Res. 1984, 17, 410, (b) Caramella, P.; Grünanger, P. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: Chichester, 1984; Vol. 1, p 291. (c) Curran, D. P. Adv. Cycloaddition 1988, 1, 129.
20. For selected reviews, see: (a) Kozikowski, A. P. Acc. Chem Res. 1984, 17, 410, (b) Caramella, P.; Grünanger, P. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: Chichester, 1984; Vol. 1, p 291. (c) Curran, D. P. Adv. Cycloaddition 1988, 1, 129.
21. Pitha, J.; Ts'O, P. O. P. J. Org. Chem. 1968, 33, 1341.
22. Carrea, G.; De Amici, M.; DeMichei, C.; Cateni; F.; Liverani, P.; Carnielle, M.; Riva, S. Tetrahedron: Asymmetry 1993, 4, 1063.
23. (a) Lapienis, G.; Penczek, S. J. Polym. Sci. Polym. Chem. 1990, 28, 1519.
24. (b) Ueda, N.; Kondo, K.; Kono, M.; Takemoto, K.; Imoto, M. Makromol. Chem. 1968, 120, 13.
25. Nishimura, T.; Iwai, I. Chem. Pharm. Bull. Tokyo 1964, 12, 352.
26. Kaye, H.; Chang, S.-H. Tetrahedron 1970, 26, 1369.
27. Thymine was the only product isolated upon treatment of thymidine analog 7b with methanolic ammonia at room temperature for 4 h. Cytosine was similarly obtained by the use of 7d.
28. (a) Larsen, K. E.; Torssell, K. B. G. Tetrahedron 1984, 40, 2985.
29. (b) Stevens, R. V.; Albizati, K. F. Tetrahedron Lett. 1984, 25, 4587.
30. (c) De Sarlo, F.; Brandi, A. J. Heterocycl. Chem. 1983, 20, 1505.