Synthesis and antiviral activity of substituted quercetins

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 1, 2012, Pages 353-356

  Thapa, Mahendra ^a   Kim, Yunjeong ^a   Desper, John ^a   Chang, Kyeong Ok ^a   Hua, Duy H ^a  

^a KANSAS STATE UNIVERSITY   (United States)

Author keywords

Antiviral activity; Influenza virus; Porcine H1N1 strain; Quercetin 3 gallate; Substituted quercetins

Indexed keywords

EPIGALLOCATECHIN GALLATE; ESTER DERIVATIVE; HYDROXYL GROUP; ISOQUERCETIN; QUERCETIN; QUERCETIN 3 GALLATE; QUERCETIN DERIVATIVE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DOSE RESPONSE; DRUG STRUCTURE; DRUG SYNTHESIS; INFLUENZA VIRUS A H1N1; NONHUMAN; VIRUS STRAIN;

ANIMALS; ANTIVIRAL AGENTS; CATECHIN; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, CHEMICAL; MOLECULAR CONFORMATION; ORTHOMYXOVIRIDAE; QUERCETIN; SWINE; VIRUS DISEASES;

ANIMALIA; ORTHOMYXOVIRIDAE; SUS;

EID: 84655169155     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.10.119     Document Type: Article

References (19)

1. C.A. Russell, T.C. Jones, I.G. Barr, N.J. Cox, R.J. Garten, V. Gregory, I.D. Gust, A.W. Hampson, A.J. Hay, A.C. Hurt, J.C. de Jong, A. Kielso, A.I. Klimov, T. Kageyama, N. Komadina, A.S. Lapedes, Y.P. Lin, A. Mosterin, M. Obuchi, T. Odagiri, A.D. Osterhaus, G.F. Rimmelzwaan, M.W. Shaw, E. Skepner, K. Stohr, M. Tashiro, R.A. Fouchier, and D.J. Smith Vaccine 26 2008 D31
2. A.-L. Liu, H.-D. Wang, S.M. Lee, Y.-T. Wang, and G.-H. Du Bioorg. Med. Chem. 16 2008 7141
3. C.-W. Lin, F.-J. Tsai, C.-H. Tsai, C.-C. Lai, L. Wan, T.-Y. Ho, C.-C. Hsieh, and P.-D.L. Chao Antiviral Res. 68 2005 36
4. Y.B. Ryu, J.H. Kim, S.-J. Park, J.S. Chang, M.-C. Rho, K.-H. Bae, K.H. Park, and W.S. Lee Bioorg. Med. Chem. Lett. 20 2010 971
5. L. Chen, J. Li, C. Luo, H. Liu, W. Xu, G. Chen, O.W. Liew, W. Zhu, C.M. Puah, X. Shen, and H. Jiang Bioorg. Med. Chem. 14 2006 8295
6. J.J. Choi, J.H. Song, K.S. Park, and D.H. Kwon Eur. J. Pharm. Sci. 37 2009 329
7. Y. Kim, S. Narayanan, and K.-O. Chang Antiviral Res. 88 2010 227
8. J.-M. Song, K.-H. Lee, and B.-L. Seong Antiviral Res. 68 2005 66
9. D.G. Nagle, D. Ferreira, and Y.-D. Zhou Phytochemistry 67 2006 1849
10. M. Roth, B.N. Timmermann, and B. Hagenbuch Drug Metab. Dispos. 39 2011 920
11. Soares-Da-Silva, P. M. V. A. PCT Int. Appl. WO 2004/084886, 2004, 36 pages.
12. H. Huang, Q. Jia, J. Ma, G. Qin, Y. Chen, Y. Xi, L. Lin, W. Zhu, J. Ding, H. Jiang, and H. Liu Eur. J. Med. Chem. 44 2009 1982
13. F. Belin, P. Barthelemy, K. Ruiz, J.M. Lacombe, and B. Pucci Helv. Chim. Acta 86 2003 247
14. K. Hayashi, Y. Hamada, and T. Shioiri Tetrahedron Lett. 33 1992 5075
15. K. Yamada, M. Ikezaki, N. Umino, H. Ohtsuka, N. Itoh, K. Ikezawa, A. Kiyomoto, and T. Iwakuma Chem. Pharm. Bull. 29 1981 744
16. R.E. Wang, J.L.-F. Kao, C.A. Hilliard, R.K. Pandita, J.L. Roti Roti, C.R. Hunt, and J.-S. Taylor J. Med. Chem. 52 2009 1912
17. E. Kaji, and S. Zen Bull. Chem. Soc. Jpn. 46 1973 337
18. A. Shi, T.A. Nguyen, S.K. Battina, S. Rana, D.J. Takemoto, P.K. Chiang, and D.H. Hua Bioorg. Med. Chem. Lett. 18 2008 3364
19. The authors have deposited atomic coordinates for the structures, compound 32 with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 175022. The coordinates can be obtained on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.