Syntheses of triazole-modified zanamivir analogues via click chemistry and anti-AIV activities

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 19, 2006, Pages 5009-5013

  Li, Jian ^a   Zheng, Mingyue ^a   Tang, Wei ^a   He, Pei Lan ^a   Zhu, Weiliang ^a   Li, Tianxian ^b   Zuo, Jian Ping ^a   Liu, Hong ^a   Jiang, Hualiang ^a,c  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b WUHAN INSTITUTE OF VIROLOGY   (China)

^c EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Avian influenza virus; Click chemistry; Molecular modeling; Zanamivir analogues

Indexed keywords

ANTIVIRUS AGENT; OSELTAMIVIR; SIALIDASE INHIBITOR; TRIAZOLE DERIVATIVE; ZANAMIVIR;

ANTIVIRAL ACTIVITY; ARTICLE; AVIAN INFLUENZA; BINDING AFFINITY; CHEMICAL REACTION; CHEMISTRY; DRUG SYNTHESIS; INFLUENZA VIRUS; MOLECULAR MODEL;

ANTIVIRAL AGENTS; ENZYME INHIBITORS; GUANIDINES; HUMANS; INFLUENZA A VIRUS, H5N1 SUBTYPE; INFLUENZA, HUMAN; MODELS, MOLECULAR; NEURAMINIDASE; PYRANS; SIALIC ACIDS; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES; ZANAMIVIR;

AVIAN INFLUENZA VIRUS;

EID: 33747624715     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.07.047     Document Type: Article

References (30)

1. Enserink M. Science 311 (2006) 932
2. Wong S.S.Y., and Yuen K.Y. Chest 129 (2006) 156
3. Ungchusak K., Auewarakul P., Dowell S.F., Kitphati R., Auwanit W., Puthavathana P., Uiprasertkul M., Boonnak K., Pittayawonganon C., Cox N.J., Zaki S.R., Thawatsupha P., Chittaganpitch M., Khontong R., Simmerman J.M., and Chunsutthiwat S. N. Eng. J. Med. 352 (2005) 333
4. Hayden F.G., and Couch R.B. Rev. Med. Virol. 2 (1992) 89
5. von Itzstein M., Wu W.Y., Kok G.B., Pegg M.S., Dyason J.C., Jin B., Phan T.V., 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
6. Woods J.M., Bethell R.C., Coates J.A., Healy N., Hiscox S.A., Pearson B.A., Ryan D.M., Tilling J., Walcott S.M., and Penn C.R. Antimicrob. Agents Chemother. 37 (1993) 1473
7. Kim C.U., Lew W., Williams M.A., Wu H., Zhang L., Chen X., Escarpe P.A., Mendel D.B., Laver W.G., and Stevens R.C. J. Med. Chem. 41 (1998) 2451
8. Mendel D.B., Tai C.Y., Escarpe P.A., Li W., Sidwell R.W., Huffman J.H., Sweet C., Jakeman K.J., Merson J., Lacy S.A., Lew W., Williams M.A., Zhang L., Chen M.S., Bischofberger N., and Kim C.U. Antimicrob. Agents Chemother. 42 (1998) 640
9. Smith P.W., Sollis S.L., Howes P.D., Cherry P.C., Starkey I.D., Cobley K.N., Weston H., Scicinski J., Merritt A., Whittington A., Wyatt P., Taylor N., Green D., Bethell R., Madar S., Fenton R.J., Morley P.J., Pateman T., and Beresford A. J. Med. Chem. 41 (1998) 787
10. Taylor N.R., Cleasby A., Singh O., Skarzynski T., Wonacott A.J., Smith P.W., Sollis S.L., Howes P.D., Cherry P.C., Bethell R., Colman P., and Varghese J. J. Med. Chem. 41 (1998) 798
11. Honda T., Masuda T., Yoshida S., Arai M., Kobayashi Y., and Yamashita M. Bioorg. Med. Chem. Lett. 12 (2002) 1921
12. Honda T., Masuda T., Yoshida S., Arai M., Kaneko S., and Yamashita M. Bioorg. Med. Chem. Lett. 12 (2002) 1925
13. Macdonald S.J., Cameron R., Demaine D.A., Fenton R.J., Foster G., Gower D., Hamblin J.N., Hamilton S., Hart G.J., Hill A.P., Inglis G.G., Jin B., Jones H.T., McConnell D.B., McKimm-Breschkin J., Mills G., Nguyen V., Owens I.J., Parry N., Shanahan S.E., Smith D., Watson K.G., Wu W.Y., and Tucker S.P. J. Med. Chem. 48 (2005) 2964
14. Woodhall T., Williams G., Berry A., and Nelson A. Angew. Chem. Int. Ed. 44 (2005) 2109
15. Woodhall T., Williams G., Berry A., and Nelson A. Org. Biomol. Chem. 3 (2005) 1795
16. Kolb H.C., Finn M.G., and Sharpless K.B. Angew. Chem. Int. Ed. 40 (2001) 2004
17. Kolb H.C., and Sharpless K.B. Drug Discov. Today 8 (2003) 1128
18. Sivakumar K., Xie F., Cash B.M., Long S., Barnhill H.N., and Wang Q. Org. Lett. 6 (2004) 4603
19. Best M.D., Brik A., Chapman E., Lee L.V., Cheng W.C., and Wong C.H. Chem. BioChem. 5 (2004) 811
20. Brik A., Alexandratos J., Lin Y.C., Elder J.H., Olson A.J., Wlodawer A., Goodsell D.S., and Wong C.H. Chem. BioChem. 6 (2005) 1167
21. Huisgen R. In: Padwa A. (Ed). 1,3-Dipolar Cycloaddition Chemistry vol. 1 (1984), Wiley, Pergamon 1-176
22. Martin R., Witte K.L., and Wong C.H. Bioorg. Med. Chem. 6 (1998) 1283
23. Chandler M., Bamford M.J., Conroy R., Lamont B., Patel B., Patel V.K., Steeples I.P., Storer R., Weir N.G., Wright M., and Williamson C. J. Chem. Soc., Perkin Trans. 1 9 (1995) 1173
24. Scheigetz J., Zamboni R., Bernstein M.A., and Roy B. Org. Prep. Proced. Int. 27 (1995) 637
25. 50 A/H5N1 virus which are dilutions of viral stocks, various concentrations of compounds and trypsin were added. At the same time, uninfected cells and infected cells without compound were performed as controls. Antiviral efficacy of test compounds was assessed in vitro by Neutral Red (NR) uptake assay. After 2 days post-infection, cells were incubated with NR dye for 2-3 h at 37 °C. Free dye was washed from the wells and the uptake dye was quantified using a microplate reader at absorbance 540 nm. Absorbance values were expressed as percentages of controls.
26. Varghese J.N., Epa V.C., and Colman P.M. Protein Sci. 4 (1995) 1081
27. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. J. Comput. Chem. 19 (1998) 1639
28. Liu H., Huang X., Shen J., Luo X., Li M., Xiong B., Chen G., Shen J., Yang Y., Jiang H., and Chen K. J. Med. Chem. 45 (2002) 4816
29. 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
30. Stoll V., Stewart K.D., Maring C.J., Muchmore S., Giranda V., Gu Y.G., Wang G., Chen Y., Sun M., Zhao C., Kennedy A.L., Madigan D.L., Xu Y., Saldivar A., Kati W., Laver G., Sowin T., Sham H.L., Greer J., and Kempf D. Biochemistry 42 (2003) 718