Synthesis of potent pyrrolidine influenza neuraminidase inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 18, Issue 5, 2008, Pages 1692-1695

  Krueger, A Chris ^a   Xu, Yibo ^a   Kati, Warren M ^a   Kempf, Dale J ^a   Maring, Clarence J ^a   McDaniel, Keith F ^a   Molla, Akhteruzzaman ^a   Montgomery, Debra ^a   Kohlbrenner, William E ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

Influenza; Neuraminidase; Pyrrolidine

Indexed keywords

4 ACETAMIDO 5 AMINO 3 (1 ETHYLPROPOXY) 1 CYCLOHEXENE 1 CARBOXYLIC ACID; OSELTAMIVIR; PYRROLIDINE DERIVATIVE; SIALIDASE INHIBITOR; VIRUS ENZYME; ZANAMIVIR;

ARTICLE; DRUG POTENCY; DRUG SYNTHESIS; IN VITRO STUDY; INFLUENZA; INFLUENZA VIRUS A; INFLUENZA VIRUS B; NONHUMAN; PROTEIN EXPRESSION; VIRUS STRAIN;

ANTIVIRAL AGENTS; INFLUENZA A VIRUS; INFLUENZA B VIRUS; MOLECULAR STRUCTURE; NEURAMINIDASE; PYRROLIDINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 39849097016     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.01.048     Document Type: Article

References (21)

1. Murray C.J.L., Lopez A.D., Chin B., Feehan D., and Hill K.K. Lancet 368 (2006) 2211
2. Goldrick B.A., and Goetz A.M. Am. J. Infect. Control 35 (2007) 7
3. Flahault A., Vergu E., Coudeville L., and Grais R.F. Vaccine 24 (2006) 6751
4. De Clercq E., and Neyts J. Trends Pharmacol. Sci. 28 (2007) 280
5. Oxford J.S., Lambkin R., Elliot A., Daniels R., Sefton A., and Gill D. Vaccine 24 (2006) 6742
6. Moscona A. N. Engl. J. Med. 353 (2005) 1363
7. Poland G.A., Jacobson R.M., and Targonski P.V. Vaccine 25 (2007) 3057
8. Nguyen-Van-Tam J.S., and Sellwood C. J. Hosp. Infect. 65 (2007) 10
9. Oxford J.S., Novelli P., Sefton A., and Lambkin R. Antiviral Chem. Chemother. 13 (2002) 205
10. Andrawiss M. Drug Discovery Today 10 (2005) 811
11. Hileman B. Chem. Eng. News 83 (2005) 47
12. Hayden F.G. Antiviral Res. 71 (2006) 372
13. Brouillette W.J., Bajpai S.N., Ali S.M., Velu S.E., Atigadda V.R., Lommer B.S., Finley J.B., Luo M., and Air G.M. Bioorg. Med. Chem. 11 (2003) 2739
14. Kim C.U., Lew W., and Williams M.A. J. Am. Chem. Soc. 119 (1997) 681
15. von Itzstein M., Wu W.Y., Kok G.B., Pegg M.S., Dyason J.C., Jin B., van Phan T., Smythe M.L., White H.F., Oliver S.W., Colman P.M., Varghese J.N., Ryan D.M., Woods J.M., Bethell R.C., Hotham V.J., Cameron J.M., and Penn C.R. Nature 363 (1993) 418
16. Wade R.C. Structure 5 (1997) 1139
17. Maring C.J., Stoll V.S., Zhao C., Sun M., Krueger A.C., Stewart K.D., Madigan D.L., Kati W.M., Xu Y., Carrick R.J., Montgomery D.A., Kempf-Grote A., Marsh K.C., Molla A., Steffy K.R., Sham H.L., Laver W.G., Gu Y.G., Kempf D.J., and Kohlbrenner W.E. J. Med. Chem. 48 (2005) 3980
18. Gu Y.G., Xu Y., Krueger A.C., Madigan D., and Sham H.L. Tetrahedron Lett. 43 (2002) 955
19. 1H NMR and LC-MS analysis (>95% purity).
20. Kati W.M., Montgomery D., Carrick R., Gubareva L., Maring C., McDaniel K., Steffy K., Molla A., Hayden F., Kempf D., and Kohlbrenner W. Antimicrob. Agents Chemother. 46 (2002) 1014
21. DeGoey D.A., Chen H., Flosi W.J., Grampovnik D.J., Yeung C.M., Klein L.L., and Kempf D.J. J. Org. Chem. 67 (2002) 5445