Synthesis and anti-viral activity of azolo-adamantanes against influenza A virus

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 2, 2010, Pages 839-848

  Zarubaev, Vladimir V ^a   Golod, Efim L ^b   Anfimov, Pavel M ^a   Shtro, Anna A ^a   Saraev, Victor V ^b   Gavrilov, Alexey S ^b   Logvinov, Alexander V ^b   Kiselev, Oleg I ^a  

^a Research Institute of Influenza   (Russian Federation)

^b ST PETERSBURG STATE INSTITUTE OF TECHNOLOGY TECHNICAL UNIVERSITY   (Russian Federation)

Author keywords

Adamantane derivatives; Antivirals; Azoles; Influenza virus

Indexed keywords

1 (1 ADAMANTYL) 1,2,4 TRIAZOLE; 1 (1 ADAMANTYL) 3 CHLORO 1,2,4 TRIAZOLE; 1 (1 ADAMANTYL) 3,5 DIMETHYLPYRAZOL 4 AMINE; 1 (1 ADAMANTYL) 4 BROMO 3 CARBOXYPYRAZOLE; 1 (1 ADAMANTYL) TETRAZOLE; 1 (1 ADAMANTYL)TETRAZOL 5 THIONE; 1 (3 AMINO 1 ADAMANTYL) 1,2,4 TRIAZOLE HYDROCHLORIDE; 1 (3 AMINO 1 ADAMANTYL) 3 BROMO 1,2,4 TRIAZOLE HYDROCHLORIDE; 1 [3 (1 AMINOETHYL) 1 ADAMANTYL] 3 CHLORO 1,2,4 TRIAZOLE HYDROCHLORIDE; 1 [3 (1 AMINOETHYL) 1 ADAMANTYL] 3 METHYL 1,2,4 TRIAZOLE DIHYDROCHLORIDE; 1 [3 (1 AMINOETHYL) 1 ADAMANTYL] 3 NITRO 1,2,4 TRIAZOLE HYDROCHLORIDE; 2 (1 ADAMANTYL) 5 BUTOXYCARBONYLMETHYLTETRAZOLE; 2 (1 ADAMANTYL) 5 CARBOXYMETHYLTETRAZOLE; 2 (1 ADAMANTYL) 5 ETHOXYCARBONYLMETHYLTETRAZOLE; 2 (1 ADAMANTYL) 5 METHYLTETRAZOLE; 2 (1 ADAMANTYL) TETRAZOLE: 2 (1 ADAMANTYL) TETRAZOLE; 2 (3 AMINO 1 ADAMANTYL) 5 ETHOXYCARBONYLMETHYLTETRAZOLE HYDROCHLORIDE; 2 (3 AMINO 1 ADAMANTYL) 5 ETHYLTETRAZOLE HYDROCHLORIDE; 2 (3 AMINO 1 ADAMANTYL) 5 METHYLTETRAZOLE HYDROCHLORIDE; 2 (3 AMINO 1 ADAMANTYL) TETRAZOLE; 2 [3 (1 AMINOETHYL) 1 ADAMANTYL] 5 ETHYLTETRAZOLE HYDROCHLORIDE; 2 [3 (1 AMINOETHYL) 1 ADAMANTYL] 5 METHYLTETRAZOLE HYDROCHLORIDE; 2 [3 (1 AMINOETHYL) 1 ADAMANTYL] TETRAZOLEHYDROCHLORIDE; 2[2 (1 ADAMANTYL) TETRAZOL 5 YL] N (2 HYDROXYETHYL)ACETAMIDE; 2[2 (1 ADAMANTYL) TETRAZOL 5 YL]ACETOHYDRAZIDE; [2 (1 ADAMANTYL)TETRAZOLYL 5](TETRAZOLYL 5)METHANE; ADAMANTANE DERIVATIVE; DI[2 (1 ADAMANTYL)TETRAZOLYL 5]METHANE; TETRAZOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG INHIBITION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; INFLUENZA VIRUS A; NONHUMAN; VIRUS INHIBITION;

ADAMANTANE; ANIMALS; ANTIVIRAL AGENTS; AZOLES; CELL LINE; DOGS; INFLUENZA A VIRUS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

INFLUENZA A VIRUS; ORTHOMYXOVIRIDAE;

EID: 76449097553     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.11.047     Document Type: Article

References (51)

1. World Health Organization, Influenza: Report by the Secretariat. World Health Assembly, WHO, Geneva, A56/23, 2004.
2. DeClercq E. J. Clin. Virol. 22 (2001) 73
3. Scholtissek C., Quack G., Klenk H.D., and Webster R.G. Antiviral Res. 37 (1998) 83
4. Lackenby A., Thompson C.I., and Democratis D. J. Curr. Opin. Infect. Dis. 21 (2008) 626
5. Tomassini J.E., Davies M.E., Hastings J.C., Lingham R., Mojena M., Raghoobar S.L., Singh S.B., Tkacz J.S., and Goetz M.A. Antimicrob. Agents Chemother. 40 (1996) 1189
6. Tomassini J., Selnick H., Davies M.E., Armstrong M.E., Baldwin J., Bourgeois M., Hastings J., Hazuda D., Lewis J., and McClements W. Antimicrob. Agents Chemother. 38 (1994) 2827
7. Hastings J.C., Selnick H., Wolanski B., and Tomassini J.E. Antimicrob. Agents Chemother. 40 (1996) 1304
8. Parkes K.E., Ermert P., Fassler J., Ives J., Martin J.A., Merrett J.H., Obrecht D., Williams G., and Klumpp K. J. Med. Chem. 46 (2003) 1153
9. Cianci C., Chung T.D.Y., Meanwell N., Putz H., Hagen M., Colonno R.J., and Krystal M. Antiviral Chem. Chemother. 7 (1996) 353
10. Furuta Y., Takahashi K., Fukuda Y., Kuno M., Kamiyama T., Kozaki K., Nomura N., Egawa H., Minami S., Watanabe Y., Narita H., and Shiraki K. Antimicrob. Agents Chemother. 46 (2002) 977
11. Nakazawa M., Kadowaki S., Watanabe I., Kadowaki Y., Takei M., and Fukuda H. Antiviral Res. 78 (2008) 194
12. Plotch S.J., O'Hara B., Morin J., Palant O., LaRocque J., Bloom J.D., Lang S.A., DiGrandi M.J., Bradley M., Nilakantan R., and Gluzman Y. J. Virol. 73 (1999) 140
13. Luo G., Torri A., Harte W.E., Danetz S., Cianci C., Tiley L., Day S., Mullaney D., Yu K.L., Ouellet C., Dextraze P., Meanwell N., Colonno R., and Krystal M. J. Virol. 71 (1997) 4062
14. Colacino J.M., DeLong D.C., Nelson J.R., Spitzer W.A., Tang J., Victor F., and Wu C.Y. Antimicrob. Agents Chemother. 34 (1990) 2156
15. Stamatiou G., Foscolos G.B., Fytas G., Kolocouris A., Kolocouris N., and De Clercq E. Bioorg. Med. Chem. 11 (2003) 5485
16. Lin T.-I., Heider H., and Schroeder C. J. Gen. Virol. 78 (1997) 767
17. Kolocouris A., Kolocouris N., Foscolos G.B., and De Clercq E. J. Med. Chem. 39 (1996) 3310
18. Zoidis G., Foscolos G.B., Fytas G., Padalko E., DeClercq E., and Kolocouris N. Bioorg. Med. Chem. 14 (2006) 3341
19. Zoidis G., Kolocouris N., Foscolos G.B., Kolocouris A., Fytas G., Padalko E., and DeClercq E. Antiviral Chem. Chemother. 14 (2003) 153
20. Kolocouris A., Foscolos G.B., Fytas G., Kolocouris N., and DeClercq E. Bioorg. Med. Chem. Lett. 9 (1999) 3465
21. Stamatiou G., Kolocouris A., Kolocouris N., Fytas G., Foscolos G.B., and De Clercq E. Bioorg. Med. Chem. Lett. 11 (2001) 2137
22. Kolocouris N., Foscolos G.B., Kolocouris A., Fytas G., and De Clercq E. J. Med. Chem. 37 (1994) 2896
23. Stylinakis I., Kolocouris N., Kolocouris A., Fytas G., Foscolos G.B., Padalko E., and De Clercq E. Bioorg. Med. Chem. Lett. 13 (2000) 1699
24. Kolocouris N., Zoidis G., Foscolos G.B., Fytas G., Prathalingham S.R., Kelly J.M., Naesens L., and De Clercq E. Bioorg. Med. Chem. Lett. 17 (2007) 4358
25. Zoidis G., Tsotinis A., Kolocouris N., Kelly J.M., Prathalingham S.R., Naesens L., and De Clercq E. Org. Biomol. Chem. 6 (2008) 3177
26. Zoidis G., Kolocouris N., Naesens L., and De Clercq E. Bioorg. Med. Chem. 17 (2009) 1534
27. Saraev V.V., and Golod E.L. Russ. J. Org. Chem. 33 (1997) 571
28. Saraev V.V., Gavrilov A.A., and Golod E.L. Russ. J. Org. Chem. 35 (1999) 1069
29. Saraev V.V., Kanakina T.P., Pevzner M.S., Golod E.L., Ugrak B.I., and Kachala V.V. Russ. Chem. Heterocycl. Compd. 32 (1996) 928
30. Gavrilov A.S., Golod E.L., Kachala V.V., and Ugrak B.I. Russ. J. Org. Chem. 35 (1999) 1234
31. Gavrilov A.S., Golod E.L., Kachala V.V., and Ugrak B.I. Russ. J. Org. Chem. 37 (2001) 1741
32. Gavrilov A.S., Kachala V.V., Kuz'mina N.E., and Golod E.L. Russ. J. Gen. Chem. 74 (2004) 752
33. Tsypin V.G., Kachala V.V., Ugrak B.I., and Golod E.L. Russ. J. Org. Chem. 38 (2002) 90
34. Amandurdyeva A.D., Saraev V.V., Kuz'mina N.E., and Golod E.L. Russ. J. Gen. Chem. 74 (2004) 1277
35. Amandurdyeva A.D., Saraev V.V., Polyakova I.N., and Golod E.L. Russ. J. Gen. Chem. 75 (2005) 130
36. Amandurdyeva A.D., Saraev V.V., Polyakova I.N., and Golod E.L. Russ. J. Gen. Chem. 75 (2005) 1475
37. Gaponik P.N., Karavay V.P., and Grigor'ev Yu.V. Russ. Chem. Heterocycl. Compd. 21 (1985) 1422 Rus.
38. Chakrabarti J.K., Foulis M.J., and Szinal S.S. Tetrahedron Lett. 60 (1968) 6249
39. Altland H.W. J. Org. Chem. 41 (1976) 3395
40. Logvinov A.V., Saraev V.V., Polyakova I.N., Strelenko Yu.A., and Golod E.L. Russ. J. Gen. Chem. 77 (2007) 2186
41. Kozeletskaia K.N., Grinbaum E.B., Zhamsrangiin M., Burmistrova V.V., and Kiselev O.I. Vopr. Virusol. 35 (1990) 289
42. Hayden F.G. Am. J. Med. 17 (1997) 55
43. Stouffer A.L., Acharya R., Salom D., Levine A.S., Di Costanzo L., Soto C.S., Tereshko V., Nanda V., Stayrook S., and DeGrado W.F. Nature 451 (2008) 596
44. Schnell J.R., and Chou J.J. Nature 451 (2008) 591
45. White L.K., Yoon J.-J., Lee J.K., Sun A., Du Y., Fu H., Snyder J.P., and Plemper R.K. Antimicrob. Agents Chemother. 51 (2007) 2293
46. Finnegon W.G., Henry R.A., and Lofguist R. J. Am. Chem. Soc. 80 (1958) 3908
47. Lieber E., and Ramachandran J. Can. J. Chem. 37 (1959) 101
48. Koreneva A.P., and Koldobskii G.I. Russ. J. Org. Chem. 35 (1999) 1511
49. Gol'tsberg M.A., Koldobskii G.I., and Tetrazoles. Russ. J. Org. Chem. 32 (1996) 1194
50. Mosmann T. J. Immunol. Methods 65 (1983) 55
51. Rimmelzwaan G.F., Baars M., Claas E.C.J., and Osterhaus A.D.M.E. J. Virol. Methods 74 (1998) 57