Antiviral activity of novel 2'-fluoro-6'-methylene-carbocyclic adenosine against wild-type and drug-resistant hepatitis B virus mutants

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 21, 2011, Pages 6328-6331

  Wanga, Jianing ^a   Singh, Uma S ^a   Rawal, Ravindra K ^a   Sugiyama, Massaya ^b   Yoo, Jakyung ^a   Jha, Ashok K ^a   Scroggin, Melissa ^a   Huang, Zhuhui ^c   Murray, Michael G ^c   Govindarajan, Rajgopal ^a   Tanaka, Yasuhito ^b   Korba, Brent ^d   Chu, Chung K ^a  

^a UNIVERSITY OF GEORGIA   (United States)

^b NAGOYA CITY UNIVERSITY GRADUATE SCHOOL OF MEDICAL SCIENCES   (Japan)

^c SOUTHERN RESEARCH INSTITUTE   (United States)

^d GEORGETOWN UNIVERSITY MEDICAL CENTER   (United States)

Author keywords

Anti HBV; Carbocyclic nucleoside; Drug resistant

Indexed keywords

2' FLUORO 6' METHYLENE CARBOCYCLIC ADENOSINE; ADEFOVIR; ANTIVIRUS AGENT; CLEVUDINE; CLOFARABINE; ENTECAVIR; LAMIVUDINE; NUCLEOSIDE PHOSPHORYLASE; PHENYLALANINE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ANTIVIRAL RESISTANCE; ARTICLE; BIOTRANSFORMATION; CHEMICAL INTERACTION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DEAMINATION; DRUG BINDING; DRUG DEGRADATION; DRUG EFFICACY; DRUG POTENCY; HEPATITIS B VIRUS; HYDROGEN BOND; MOLECULAR MODEL; NONHUMAN; STRUCTURE ACTIVITY RELATION; WILD TYPE;

HEPATITIS B VIRUS;

EID: 80054779528     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.08.113     Document Type: Article

References (23)

1. Sorrell, M. F.; Belongia, E. A.; Costa, J.; Gareen, I. F.; Grem, J. L.; Inadomi, J. M.; Kern, E. R.; McHugh, J. A.; Petersen, G. M.; Rein, M. F. Hepatology 2009, 49, S4.
2. Ganem, D.; Prince, A. M. N. Eng. J. Med. 2004, 350, 1118.
3. Delaney, W. E.; Locarnini, S.; Shaw, T. Antiviral Chem. Chemother. 2001, 12, 1.
4. Genovesi, E. V.; Lamb, L.; Medina, I.; Taylor, D.; Seifer, M.; Innaimo, S.; Colonno, R. J.; Standring, D. N.; Clark, J. M. Antimicrob. Agents Chemother. 1998, 42, 3209.
5. Suzuki, Y.; Suzuki, F.; Kawamura, Y.; Yatsuji, H.; Sezaki, H.; Hosaka, T.; Akuta, N.; Kobayashi, M.; Saitoh, S.; Arase, Y. J. Gastroenterol. Hepatol. 2009, 24, 429.
6. Mukaide, M.; Tanaka, Y.; Shin-I, T.; Yuen, M. F.; Kurbanov, F.; Yokosuka, O.; Sata, M.; Karino, Y.; Yamada, G.; Sakaguchi, K. Antimicrob. Agents Chemother. 2010, 54, 882.
7. Crimmins, M. T. Tetrahedron 1998, 54, 9229.
8. Ferrero, M.; Gotor, V. Chem. Rev. 2000, 100, 4319.
9. Wang, J.; Jin, Y.; Rapp, K. L.; Bennett, M.; Schinazi, R. F.; Chu, C. K. J. Med. Chem. 2005, 48, 3736.
10. Chu, C. K.; Ma, T.; Shanmuganathan, K.; Wang, C.; Xiang, Y.; Pai, S. B.; Yao, G. Q.; Sommadossi, J. P.; Cheng, Y. C. Antimicrob. Agents Chemother. 1995, 39, 979.
11. Sharon, A.; Jha, A. K.; Chu, C. K. In Analogue-based Drug Discovery II; Fisher, J., Ganellin, C. R., Eds.; WILEY-VCH GmbH & Co., KGaA: Weinheim, 2010; p 383.
12. Montgomery, J. A.; Shortnacy-Fowler, A. T.; Clayton, S. D.; Riordan, J. M.; Secrist, J. A. J. Med. Chem. 1992, 35, 397.
13. Gadthula, S.; Rawal, R. K.; Sharon, A.; Wu, D.; Korba, B.; Chu, C. K. Bioorg. Med. Chem. Lett. 2011, 21, 3982.
14. Dey, S.; Garner, P. J. Org. Chem. 2000, 65, 7697.
15. Korba, B. E.; Gerin, J. L. Antiviral Res. 1992, 19, 55.
16. Iyer, R. P.; Jin, Y.; Roland, A.; Morrey, J. D.; Mounir, S.; Korba, B. Antimicrob. Agents Chemother. 2004, 48, 2199.
17. Stoeckler, J. D.; Bell, C. A.; Parks, R. E., Jr.; Chu, C. K.; Fox, J. J.; Ikehara, M. Biochem. Pharmacol. 1982, 31, 1723.
18. Villet, S.; Ollivet, A.; Pichoud, C.; Barraud, L.; Villeneuve, J.-P.; Trépo, C.; Zoulim, F. J. Hepatol. 2007, 46, 531.
19. Walsh, A. W.; Langley, D. R.; Colonno, R. J.; Tenney, D. J. PloS one 2010, 5, e9195.
20. Schrodinger Suit 2006; LLC, N. Y., NY 2005.
21. http://www.pdb.org, RCSB Protein Data Bank.
22. Sharon, A.; Chu, C. K. Antiviral Res. 2008, 80, 339.
23. Glide, version 4.5; Schrodinger LLC: New York, 2007.