Bitriazolyl acyclonucleosides with antiviral activity against tobacco mosaic virus

Tetrahedron Letters

Volumn 49, Issue 17, 2008, Pages 2804-2809

  Li, Wei ^a   Xia, Yi ^a,b   Fan, Zhijin ^c   Qu, Fanqi ^a   Wu, Qiongyou ^a,d   Peng, Ling ^a,b  

^a WUHAN UNIVERSITY   (China)

^b AIX MARSEILLE UNIVERSITÉ   (France)

^c NANKAI UNIVERSITY   (China)

^d BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

Acyclonucleosides; Anti TMV; Bitriazoly compounds; Tobacco mosaic virus; Triazole nucleosides

Indexed keywords

1 [(2 HYDROXYETHOXY)METHYL] 6 (PHENYLTHIO)THYMINE; ACICLOVIR; ACYCLIC NUCLEOSIDE; ANTIVIRUS AGENT; BITRIAZOLYL ACYCLONUCLEOSIDE; BITRIAZOLYL RIBONUCLEOSIDE; FLUCONAZOLE; RIBAVIRIN; UNCLASSIFIED DRUG;

AMMONOLYSIS; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; NONHUMAN; TOBACCO MOSAIC VIRUS;

TOBACCO MOSAIC VIRUS;

EID: 40949095201     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.02.139     Document Type: Article

References (31)

1. Sidwell R.W., Huffman J.H., Khare G.P., Allen L.B., Witkowski J.T., and Robins R.K. Science 177 (1972) 705-706
2. De Clercq E. Nature Rev. Drug Discovery 1 (2002) 13-25
3. Al-Soud Y.A., Al-Dweri M.N., and Al-Masoudi N.A. IL FARMACO 59 (2004) 775-783
4. Wan J.Q., Zhu R.Z., Xia Y., Qu F.Q., Wu Q.Y., Yang G.F., Neyts J., and Peng L. Tetrahedron Lett. 47 (2006) 6727-6731
5. Zhu R.Z., Qu F.Q., Quéléver G., and Peng L. Tetrahedron Lett. 48 (2007) 2389-2393
6. Xia Y., Qu F.Q., Li W., Wu Q.Y., and Peng L. Heterocycles 65 (2005) 345-352
7. Xia Y., Fan Z.J., Yao J.H., Liao Q., Li W., Qu F.Q., and Peng L. Bioorg. Med. Chem. Lett. 16 (2006) 2693-2698
8. Xia Y., Li W., Qu F.Q., Fan Z.J., Liu X.F., Berro C., Rauzy E., and Peng L. Org. Biomol. Chem. 5 (2007) 1695-1701
9. Schaeffer H.J., Beauchamp L., De Miranda P., Elion G.B., Bauer D.J., and Collins P. Nature 272 (1978) 583-585
10. Elion G.B., Furman P.A., Fyfe J.A., De Miranda P., Beauchamp L., and Schaeffer H.J. Proc. Natl. Acad. Sci. U.S.A. 74 (1977) 5716-5720
11. Miyasaka T., Tanaka H., Baba M., Hayakawa H., Walker R.T., Balzarini J., and De Clercq E. J. Med. Chem. 32 (1989) 2507-2509
12. Tanaka H., Takashima H., Ubasawa M., Sekiya K., Nitta I., Baba M., Shigeta S., Walker R.T., De Clercq E., and Miyasaka T. J. Med. Chem. 35 (1992) 4713-4719
13. Ren J., Esnouf R., Garman E., Somers D., Ross C., Kirby I., Keeling J., Darby G., Jones Y., Stuart D., and Stammers D. Nature Struct. Biol. 2 (1995) 293-302
14. Kolb H.C., Finn M.G., and Sharpless K.B. Angew. Chem., Int. Ed. 40 (2001) 2004-2021
15. Kolb H.C., and Sharpless K.B. Drug Discovery Today 8 (2003) 1128-1137
16. Bock V.D., Hiemstra H., and Maarseveen J.H. Eur. J. Org. Chem. (2006) 51-68
17. Moses J.E., and Moorhouse A.D. Chem. Soc. Rev. 36 (2007) 1249-1262
18. Keyser G.E., Bryant J.D., and Barrio J.R. Tetrahedron Lett. 20 (1979) 3263-3264
19. Robins M.J., and Hatfield P.W. Can. J. Chem. 60 (1982) 547-553
20. Preparation of 1 and 1′: In a solution of methyl 5-azide-1,2,4-triazole-3-carboxylate (1.25 g, 7.4 mmol) in 40 mL anhydrous acetonitrile, 0.28 g of sodium hydride (70% in mineral oil, 8.2 mmol) was added portionwise under strong stirring. When sodium hydride was completely dissolved, 1.58 mL (8.9 mmol) of 2-(chloromethoxy)ethyl benzoate was added dropwise, and the mixture was stirred at room temperature for 72 h. The reaction mixture was filtrated and the filtrate was concentrated under reduced pressure. The residue was purified on silica gel with petroleum ether/ethyl acetate (2:1, v/v), affording 1 as a white solid (1.07 g, 41.8%) and 1′ as a waxy solid (0.75 g, 29.2%).
21. Wu Q.Y., Qu F.Q., Wan J.Q., Zhu X., Xia Y., and Peng L. Helv. Chim. Acta 87 (2004) 811-819
22. 4, and concentrated. The obtained residue was purified on silica gel with petroleum ether/ethyl acetate (2:1, v/v), giving the corresponding product 2 as a white powder.
23. 2, and dried in vacuo.
24. 3OH (30/:1, v/v).
25. 3OH (30:1, v/v).
26. Kallander L.S., Lu Q., Chen W., Tomaszek T., Yang G., Tew D., Meek T.D., Hofmann G.A., Schulz-Pritchard C.K., Smith W.W., Janson C.A., Ryan M.D., Zhang G., Johanson K.O., Kirkpatrick R.B., Ho T.F., Fisher P.W., Mattern M.R., Johnson R.K., Hansbury M.J., Winkler J.D., Ward K.W., Veber D.F., and Thompson S.K. J. Med. Chem. 48 (2005) 5644-5647
27. Nowak I., and Robins M.J. J. Org. Chem. 71 (2006) 8876-8883
28. Liu J., and Robins M.J. Org. Lett. 6 (2004) 3421-3423
29. Robins M.J., Miles R.W., Samano M.C., and Kaspar R.L. J. Org. Chem. 66 (2001) 8204-8210
30. Zhong M., Nowak I., and Robins M.J. J. Org. Chem. 71 (2006) 7773-7779
31. An T.Y., Huang R.Q., Yang Z.D., Zhang K., Li G.R., Yao Y.C., and Gao J. Phytochemistry 58 (2001) 1267-1269