Synthesis of tamiflu and its phosphonate congeners possessing potent anti-influenza activity

Journal of the American Chemical Society

Volumn 129, Issue 39, 2007, Pages 11892-11893

  Shie, Jiun Jie ^a   Fang, Jim Min ^a,b   Wang, Shi Yun ^a   Tsai, Keng Chang ^a   Cheng, Yih Shyun E ^a   Yang, An Suei ^a   Hsiao, Shih Chia ^a   Su, Ching Yao ^a   Wong, Chi Huey ^a,c  

^a GENOMICS RESEARCH CENTER   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^c SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

OSELTAMIVIR; PHOSPHONIC ACID DERIVATIVE; SIALIDASE INHIBITOR; ZANAMIVIR;

ARTICLE; DRUG BIOAVAILABILITY; DRUG EFFICACY; DRUG POTENCY; DRUG SAFETY; DRUG SYNTHESIS; HUMAN; INFLUENZA; MOLECULAR MODEL;

ANIMALS; ANTIVIRAL AGENTS; CELL LINE; DOGS; ENZYME INHIBITORS; INFLUENZA A VIRUS, H1N1 SUBTYPE; INFLUENZA A VIRUS, H5N1 SUBTYPE; KINETICS; MODELS, MOLECULAR; NEURAMINIDASE; OSELTAMIVIR; PHOSPHONIC ACIDS;

EID: 34848839869     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja073992i     Document Type: Article

References (26)

1. (a) Kaye, D.; Pringle, C. R. Clin. Infect. Dis. 2005, 40, 108.
2. (b) Beigel, J. H.; Farrar, J.; Han, A. M.; Hayden, F. G.; de Jong, M. D.; Lochindarat, S.; Tien, N. T. K.; Hien, N. T.; Hien, T. T.; Nicoll, A.; Touch, S.; Yuen, K.-Y. N. Engl. J. Med. 2005, 353, 1374.
3. (a) Moscona, A. N. Engl. J. Med. 2005, 353, 1363.
4. (b) Ward, P.; Samll, I.; Smith, J.; Suter, P.; Dutkowski, R. J. Antimicrob. Chemother. 2005, 55 (Suppl. S1), i5.
5. (c) De Clercq, E. Nature Rev. Drug Discov. 2006, 5, 1015.
6. (a) von Itzstein, M.; et al. Nature 1993, 363, 418.
7. (b) Lew, W.; Chen, X.; Kim, C. U. Curr. Med. Chem. 2000, 7, 663.
8. (c) Russell, R. J.; Haire, L. F.; Stevens, D. J.; Collins, P. J.; Lin, Y. P.; Blackburn, G. M.; Hay, A. J.; Camblin, S. J.; Skehel, J. J. Nature 2006, 443, 45.
9. (a) Kim, C. U.; Lew, W.; Williams, M. A.; Liu, H.; Zhang, L.; Swaminathan, S.; Bischofberger, N.; Chen, M. S.; Mendel, D. B.; Tai, C. Y.; Laver, W. G.; Stevens, R. C. J. Am. Chem. Soc. 1997, 119, 681.
10. (b) Rohloff, J. C.; Kent, K. M.; Postich, M. J.; Becker, M. W.; Chapman, H. H.; Kelly, D. E.; Lew, W.; Louie, M. S.; McGee, L. R.; Prisbe, E. J.; Schultze, L. M.; Yu, R. H.; Zhang, L. J. Org. Chem. 1998, 63, 4545.
11. (c) Karpf, M.; Trussardi, R. J. Org. Chem. 2001, 66, 2044.
12. (d) Harrington, P. J.; Brown, J. D.; Foderaro, T.; Hughes, R. C. Org. Process Res. Dev. 2004, 8, 86.
13. (e) Yeung, Y.-Y.; Hong, S.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 6310.
14. (f) Fukuta, Y.; Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312.
15. (g) Farina, V.; Brown, J. D. Angew. Chem., Int. Ed. 2006, 45, 7330.
16. (h) Mita, T.; Fukuda, N.; Roca, F. X.; Kanai, M.; Shibasaki, M. Org. Lett. 2007, 9, 259.
17. (i) Yamatsugu, K.; Kamijo, S.; Suto, Y.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2007, 48, 1403.
18. (a) White, C. L.; Janakiraman, M. N.; Laver, W. G.; Philippon, C.; Vasella, A.; Air, G. M.; Luo, M. J. Mol. Biol. 1995, 245, 623.
19. (b) Streicher, H.; Meisch, J.; Bohner, C. Tetrahedron 2001, 57, 8851.
20. (c) Streicher, H. Bioorg. Med. Chem. Lett. 2004, 14, 361.
21. (d) Schug, K. A.; Lindner, W. Chem. Rev. 2005, 105, 67.
22. (e) Streicher, H.; Busseb, H. Bioorg. Med. Chem. 2006, 14, 1047.
23. Stigers, K. D.; Mar-Tang, R.; Bartlett, P. A. J. Org. Chem. 1999, 64, 8409.
24. Mai Le, Q.; et al. Nature 2005, 437, 1108.
25. Cheng, Y.-C.; Prusoff, W. H. Biochem. Pharmacol. 1973, 22, 3099.
26. Krise, J. P.; Stella, V. J. Adv. Drug Deliv. Rev. 1996, 19, 287.