Synthesis of novel analogues of zanamivir as neuraminidase inhibitors

Chinese Chemical Letters

Volumn 21, Issue 11, 2010, Pages 1338-1341

  Xiong, Rui Sheng ^a   Zhao, Qing Jie ^a   Zhu, Hang Hang ^b   Liu, Zheng ^c   Wei, Ya Bing ^b   Shen, Jing Shan ^a,c  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b NANJING TECH UNIVERSITY   (China)

^c Topharman Shanghai Co Ltd   (China)

Author keywords

Click chemistry; Triazole; Zanamivir

Indexed keywords

EID: 77957240832     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cclet.2010.06.021     Document Type: Article

References (25)

1. Gong J.Z., Xu W.F., Zhang J. Curr. Med. Chem. 2007, 14:113.
2. Colman P.M., Hoyne P.A., Lawrence M.C. J. Virol. 1993, 67:2972.
3. Zhang J., Xu W.F. Mini-Rev. Med. Chem. 2006, 6:429.
4. Varghese J.N., Epa V.C., Colman P.M. Protein Sci. 1995, 4:1081.
5. Taylor N.R., Cleasby A., Singh O., et al. J. Med. Chem. 1998, 41:798.
6. Wang G.T., Chen Y.W., Wang S., et al. J. Med. Chem. 2001, 44:1192.
7. Babu Y.S., Chand P., Bantia S., et al. J. Med. Chem. 2000, 43:3482.
8. Kim C.U., Lew W., Williams M.A., et al. J. Am. Chem. Soc. 1997, 119:681.
9. Chand P. Expert Opin. Ther. Pat. 2005, 15:1009.
10. Feder H.M. N. Engl. J. Med. 2001, 344:528.
11. Ryan D.M., Ticehurst J., Dempsey M.H. Antimicrob. Agents Chemother. 1995, 39:2583.
12. Liu Z.Y., Wang B., Zhao L.X., et al. Bioorg. Med. Chem. Lett. 2007, 17:4851.
13. Li J., Zheng M.Y., Tang W., et al. Bioorg. Med. Chem. Lett. 2006, 16:5009.
14. Masuda T., Shibuya S., Arai M., et al. Bioorg. Med. Chem. Lett. 2003, 13:669.
15. Stoll V., Stewart K.D., Maring C.J., et al. Biochemistry 2003, 42:718.
16. Smith P.W., Sollis S.L., Howes P.D., et al. Bioorg. Med. Chem. Lett. 1996, 6:2931.
17. Tindal D.J., Dyason J.C., Thomson R.J., et al. Bioorg. Med. Chem. Lett. 2007, 17:1655.
18. Zhao Q.J., Lou Y.Y., Xiong R.S., et al. Carbohydr. Res. 2008, 343:2459.
19. Kraus G.A., Roth B. J. Org. Chem. 1980, 45:4825.
20. Chan L.C., Cox B.G. J. Org. Chem. 2007, 72:8863.
21. Kolb H.C., Sharpless K.B. Drug Discov. Today 2003, 8:1128.
22. Christopher D.S., Ian R.B., Steve L., et al. Org. Biomol. Chem. 2007, 5:1559.
23. Hao C., Janet L.T., Suzanne R.A. Bioorg. Med. Chem. Lett. 2007, 17:1979.
24. Maria V.G., Maria J.A., Oscar L. Synthesis 2007, 1589.
25. The data for representative compounds: 13c: 1H NMR (400MHz, DMSO-d6): δ 7.79 (s, 1 H, CH), 5.81 (d, 1 H, J=2.4Hz, 3-H), 5.51 (dd, 1 H, J=2.0Hz, J=7.2Hz, 4-H), 4.55 (d, 1 H, J=10.8Hz, 6-H), 4.22 (m, 1 H, 5-H), 4.05 (d, 1 H, J=4.0Hz, 7-H), 2.64 (d, 3 H, J=3.6Hz, CH3), 1.92 (m, 1 H, CH), 1.76 (s, 3 H, NHAc), 0.88 (m, 2 H, CH2), 0.69 (m, 2 H, CH2); HRMS(ESI): m/z calcd. C16H20N5O62Na [M-H+2Na]+ 424.1209, found 424.1232. 13d: 1H NMR (400MHz, DMSO-d6): δ 8.63 (s, 1 H, CH), 7.82 (m, 1 H, NH), 5.91 (d, 1 H, J=2.3Hz, 3-H), 5.60 (dd, 1 H, J=1.9Hz, J=9.8Hz, 4-H), 4.58 (d, 1 H, J=11.3Hz, 6-H), 4.33 (m, 1 H, 5-H), 4.09 (s, 1 H, 7-H), 2.64 (d, 3 H, J=3.6Hz, CH3), 1.74 (s, 3 H, NHAc); HRMS(ESI): m/z calcd. C14H17N5O8Na [M+Na]+ 406.0975, found 406.0991. 13e: 1H NMR (400MHz, DMSO-d6): δ 8.28 (s, 1 H, CH), 7.03 (m, 4 H, PhH), 6.51 (d, 1 H, J=7.6Hz, NH), 5.51 (d, 2 H, J=4.5Hz, 3-H and 4-H), 4.46 (m, 1 H, CH, 6-H), 4.29 (m, 1 H, CH, 5-H), 4.05 (m, 1 H, CH, 7-H), 2.65 (d, 3 H, J=3.6Hz, CH3), 1.74 (s, 3 H, NHAc); HRMS(ESI): m/z calcd. C19H22N6O6Na [M+Na]+ 453.1499, found 453.1515.