Synthesis and anti-HIV-1 activity of carbocyclic versions of stavudine analogues using a ring-closing metathesis

Bulletin of the Korean Chemical Society

Volumn 29, Issue 9, 2008, Pages 1723-1728

  Lian, Jin Liu ^a   Ok, Hyun Ko ^a   Joon, Hee Hong ^a  

^a Chosun University   (South Korea)

Author keywords

Antiviral agents; Carbocyclic nucleoside; Claisen rearrangement; Ring closing metathesis

Indexed keywords

BIOMOLECULES; CARBON; CELL CULTURE;

ANTI-HIV-1 ACTIVITY; ANTIVIRAL ACTIVITIES; CARBOCYCLIC NUCLEOSIDES; CELL LINES; CLAISEN REARRANGEMENT; QUATERNARY CARBON; RING CLOSING METATHESIS; SYNTHETIC ROUTES;

ANTIVIRAL AGENTS;

EID: 52749094452     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2008.29.9.1723     Document Type: Article

References (25)

1. (a) Crimmins, M. T. Tetrahedron 1998, 54, 9229.
2. (b) Ariona, O.; Gómez, A. M.; López, J. C.; Plumet, J. Chem. Rev. 2007, 107, 1919.
3. Herdewijn, P.; De Clercq, E.; Balzarini, J.; Vanderhaeghe, H. J. Med. Chem. 1985, 28, 550.
4. (a) Palmer, J. L.; Abeles, R. H. J. Biol. Chem. 1979, 254, 1217.
5. (b) Ueland, P. M. Pharmacol. Rev. 1982, 34, 223.
6. Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17.
7. (a) Daluge, S. M.; Good, S. S.; Faletto, M. B.; Miller, W. H.; St Clair, M. H.; Boone, L. R.; Tisdale, M.; Parry, N. R.; Reardon, J. E.; Dornsife, R. E.; Averett, D. R.; Krenitsky, T. A. Antimicrob. Agents Chemother. 1997, 41, 1082.
8. (b) Dobkin, J. F. Infect. Med. 1999, 17, 625.
9. Parker, W. B.; Cheng, Y.-C. J. NIH. Res. 1994, 6, 57.
10. Chatis, P. A.; Crumpacker, C. S. Antimicrob. Agents Chemother. 1992, 36, 1589.
11. Maag, H.; Rydzewski, R. M.; McRoberts, M. J.; Crawford-Ruth, D.; Verheyden, J. P.; Prisbe, E. J. J. Med. Chem. 1992, 35, 1440.
12. O-Yang, C.; Wu, H. Y.; Fraser-Smith, E. B.; Walker, K. A. M. Tetrahedron Lett. 1992, 33, 37.
13. Haraguchi, K.; Takeda, S.; Tanaka, H.; Nitanda, T.; Baba, M.; Dutschman, G. E.; Cheng, Y.-C. Bioorg. Med. Chem. Lett. 2003, 13, 3775.
14. Kumamoto, H.; Nakai, T.; Haraguchi, K.; Nakamura, K. T.; Tanaka, H.; Baba, M.; Cheng, Y.-C. J. Med. Chem. 2006, 49, 7861.
15. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
16. Haines, D. R.; Tseng, C. K. H.; Marquez, V. E. J. Med. Chem. 1987, 30, 943.
17. (a) Ziegler, F. E. Chem. Rev. 1988, 88, 1423.
18. (b) Johnson, W. S.; Werthmann, L.; Bartlett, W. R.; Brockson, T. J.; Li, T. T.; Faulkner, D. J.; Peterson, M. R. J. Am. Chem. Soc. 1970, 92, 741.
19. (a) Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem. Int. Ed. 2005, 44, 4490.
20. (b) Kim, A.; Hong, J. H. Bull. Korean Chem. Soc. 2007, 28, 1545.
21. (c) Jeong, L. S.; Lee, J. A. Antiviral Chem. Chemother. 2004, 15, 235.
22. (a) Trost, B. M.; Kallander, L. S. J. Org. Chem. 1999, 64, 5427,
23. (b) Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1996, 118, 3037,
24. (c) Li, H.; Hong, J. H. Bull. Korean Chem. Soc. 2007, 28, 1645.
25. Weislow, O. S.; Kiser, R.; Fine, D. L.; Bader, J.; Shoemaker, R. H.; Boyd, M. R. J. Natl. Cancer Inst. 1989, 81, 577.