Anti-viral activity of (-)- and (+)-usnic acids and their derivatives against influenza virus A(H1N1)2009

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 23, 2012, Pages 7060-7064

  Sokolov, Dmitriy N ^a   Zarubaev, Vladimir V ^b   Shtro, Anna A ^b   Polovinka, Marina P ^a   Luzina, Olga A ^a   Komarova, Nina I ^a   Salakhutdinov, Nariman F ^a   Kiselev, Oleg I ^b  

^a N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b Influenza Research Institute   (Russian Federation)

Author keywords

Antiviral; Enantiomer; Influenza; Pandemic; Usnic acid

Indexed keywords

6 ACETYL 2 [1 (3 BROMOPHENYLAMINO)ETHYLIDINE] 7,9 DIHYDROXY 8,9B DIMETHYLDIBENZO[B,D]FURAN 1,3[2H,9BH]DIONE; 6 ACETYL 2 [1 (3 FLUOROPHENYLAMINO)ETHYLIDINE] 7,9 DIHYDROXY 8,9B DIMETHYLDIBENZO[B,D]FURAN 1,3[2H,9BH]DIONE; 6 ACETYL 2 [1 (4 FLUOROPHENYLAMINO)ETHYLIDINE] 7,9 DIHYDROXY 8,9B DIMETHYLDIBENZO[B,D]FURAN 1,3[2H,9BH]DIONE; 6 ACETYL 7,9 DIHYDROXY 8,9B DIMETHYL 2 [1 (2',2',3',3' TETRAFLUOROPROPYLAMINO)ETHYLIDENE]DIBENZO[B,D]FURAN 1,3 DIONE; ANTIVIRUS AGENT; TETRAZOLIUM; UNCLASSIFIED DRUG; USNIC ACID; USNIC ACID DERIVATIVE;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; ASSAY; CELL STRAIN; CHEMICAL MODIFICATION; DOSE RESPONSE; DRUG ISOLATION; ENANTIOMER; INFLUENZA VIRUS A H1N1; ISOMER; NITROBLUE TETRAZOLIUM TEST; NONHUMAN;

ANIMALS; ANTI-INFLAMMATORY AGENTS; ANTIVIRAL AGENTS; BENZOFURANS; CELL LINE; CELL SURVIVAL; DOGS; HUMANS; INFLUENZA A VIRUS, H1N1 SUBTYPE; MACROPHAGES; MADIN DARBY CANINE KIDNEY CELLS; MICE; NITRIC OXIDE SYNTHASE TYPE II; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRANSCRIPTION FACTOR RELA; TUMOR NECROSIS FACTOR-ALPHA;

INFLUENZAVIRUS A;

EID: 84869080640     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.09.084     Document Type: Article

References (39)

1. Y. Ghendon World Health Statistic Q 45 1992 306
2. P. Palese Nat. Med. 10 2004 S82
3. M.B. Rothberg, and S.D. Haessler Crit. Care Med. 38 2010 e91
4. M.G. Ison Curr. Opin. Virol. 1 2011 563
5. C. Scholtissek, G. Quack, H.D. Klenk, and R.G. Webster Antiviral Res. 37 1998 83
6. K. Thorlund, T. Awad, G. Boivin, and L. Thabane BMC Infect. Dis. 11 2011 134
7. S.H. Hauge, S. Dudman, K. Borgen, A. Lackenby, and O. Hungnes Emerg. Infect. Dis. 15 2009 155
8. F.G. Hayden, C.A. Sable, J.D. Connor, and J. Lane Antivir. Ther. 1 1996 51
9. J. Beigel, and M. Bray Antiviral Res. 78 2008 91
10. Y. Furuta, K. Takahashi, K. Shiraki, K. Sakamoto, D.F. Smee, D.L. Barnard, B.B. Gowen, J.G. Julander, and J.D. Morrey Antiviral Res. 82 2009 95
11. J.E. Tomassini, M.E. Davies, J.C. Hastings, R. Lingham, M. Mojena, S.L. Raghoobar, S.B. Singh, J.S. Tkacz, and M.A. Goetz Antimicrob. Agents Chemother. 40 1996 1189
12. J. Tomassini, H. Selnick, M.E. Davies, M.E. Armstrong, J. Baldwin, M. Bourgeois, J. Hastings, D. Hazuda, J. Lewis, and W. McClements Antimicrob. Agents Chemother. 38 1994 2827
13. J.C. Hastings, H. Selnick, B. Wolanski, and J.E. Tomassini Antimicrob. Agents Chemother. 40 1996 1304
14. K.E. Parkes, P. Ermert, J. Fassler, J. Ives, J.A. Martin, J.H. Merrett, D. Obrecht, G. Williams, and K. Klumpp J. Med. Chem. 46 2003 1153
15. C. Cianci, T.D.Y. Chung, N. Meanwell, H. Putz, M. Hagen, R.J. Colonno, and M. Krystal Antivir. Chem. Chemother. 7 1996 353
16. M. Nakazawa, S. Kadowaki, I. Watanabe, Y. Kadowaki, M. Takei, and H. Fukuda Antiviral Res. 78 2008 194
17. S.J. Plotch, B. O'Hara, J. Morin, O. Palant, J. LaRocque, J.D. Bloom, S.A. Lang, M.J. DiGrandi, M. Bradley, R. Nilakantan, and Y. Gluzman J. Virol. 73 1999 140
18. G. Luo, A. Torri, W.E. Harte, S. Danetz, C. Cianci, L. Tiley, S. Day, D. Mullaney, K.L. Yu, C. Ouellet, P. Dextraze, N. Meanwell, R. Colonno, and M. Krystal J. Virol. 71 1997 4062
19. J.M. Colacino, D.C. DeLong, J.R. Nelson, W.A. Spitzer, J. Tang, F. Victor, and C.Y. Wu Antimicrob. Agents Chemother. 34 1990 2156
20. H.H. Hoffmann, A. Kunz, V.A. Simon, P. Palese, and M.L. Shaw Proc. Natl. Acad. Sci. U.S.A. 108 2011 5777
21. K. Ingolfsdottir Phytochemistry 61 2002 729
22. N.B. Perry, M.H. Benn, N.J. Brennan, E.J. Burgess, G. Ellis, D.J. Galloway, S.D. Lorimer, and R.S. Tangney Lichenologist 31 1999 627
23. P. Scirpa, G. Scambia, V. Masciullo, F. Battaglia, E. Foti, R. Lopez, P. Villa, M. Malecore, and S. Mancuso Minerva Ginecol. 51 1999 255
24. Y. Yamamoto, Y. Miura, Y. Kimoshita, M. Higuchi, Y. Yamada, A. Murakami, H. Ohigashi, and K. Koshimizu Chem. Pharm. Bull. 43 1995 1388
25. Salakhutdinov, N. F.; Polovinka, M. P.; Panchenko, M.; Yu. Byull. Izobret., 2008, 5, RF Patent No. 2317,076C1.
26. V. Farina, J.T. Reeves, C.H. Senanayake, and J.J. Song Chem. Rev. 106 2006 2734
27. O.A. Luzina, M.P. Polovinka, N.F. Salakhutdinov, and G.A. Tolstikov Russ. J. Org. Chem. 45 2009 1783
28. D.N. Sokolov, O.A. Luzina, M.P. Polovinka, and N.F. Salakhutdinov Chem. Nat. Comp. 47 2011 203
29. A.A. Tazetdinova, O.A. Luzina, M.P. Polovinka, N.F. Salakhutdinov, and G.A. Tolstikov Chem. Nat. Comp. 45 2010 800
30. O.A. Luzina, M.P. Polovinka, N.F. Salakhutdinov, and G.A. Tolstikov Russ. Chem. Bull. 56 2007 1249
31. D.N. Sokolov, O.A. Luzina, M.P. Polovinka, D.V. Korchagina, Yu.V. Gatilov, and N.F. Salakhutdinov Chem. Nat. Comp. 46 2010 730
32. E. Vanderlinden, F. Göktas, Z. Cesur, M. Froeyen, M.L. Reed, C.J. Russell, N. Cesur, and L. Naesens J. Virol. 84 2010 4277
33. P. Selvam, N. Murugesh, M. Chandramohan, R.W. Sidwell, M.K. Wandersee, and D.F. Smee Antivir. Chem. Chemother. 17 2006 269
34. http://chemdb.niaid.nih.gov/CellularDetails.aspx?AIDSNO=028613&pn=1.
35. G.M. König, A.D. Wright, and S.G. Franzblau Planta Med. 66 2000 337
36. L. Campanella, M. Delfini, P. Ercole, A. Iacoangeli, and G. Risuleo Biochimie 84 2002 329
37. J.Q. Jin, C.Q. Li, and L.C. He Phytother. Res. 22 2008 1605
38. R. Pinto, S. Herold, L. Cakarova, K. Hoegner, J. Lohmeyer, O. Planz, and S. Pleschka Antiviral Res. 92 2011 45
39. T.J. Mosmann Immunol. Methods 65 1983 55