Antiviral activity of various 1-(2′-Deoxy-β- d -lyxofuranosyl), 1-(2′-Fluoro-β- d -xylofuranosyl), 1-(3′-Fluoro-β- d -arabinofuranosyl), and 2′-fluoro-2′,3′-didehydro-2′, 3′-dideoxyribose pyrimidine nucleoside analogues against duck hepatitis B virus (DHBV) and human hepatitis B virus (HBV) replication

Journal of Medicinal Chemistry

Volumn 53, Issue 19, 2010, Pages 7156-7166

  Srivastav, Naveen C ^a   Shakya, Neeraj ^a   Mak, Michelle ^a   Agrawal, Babita ^a   Tyrrell, D Lorne ^a   Kumar, Rakesh ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 DEOXY 2 FLUORO BETA DEXTRO ARABINOFURANOSYL)URACIL; 1 (2 DEOXY BETA DEXTRO LYXOFURANOSYL) 4 THIOTHYMINE; 1 (2 DEOXY BETA DEXTRO LYXOFURANOSYL) 5 BROMOURACIL; 1 (2 DEOXY BETA DEXTRO LYXOFURANOSYL) 5 CHLOROURACIL; 1 (2 DEOXY BETA DEXTRO LYXOFURANOSYL) 5 ETHYLURACIL; 1 (2 DEOXY BETA DEXTRO LYXOFURANOSYL) 5 FLUOROURACIL; 1 (2 DEOXY BETA DEXTRO LYXOFURANOSYL) 5 IODORACIL; 1 (2 DEOXY BETA DEXTRO LYXOFURANOSYL) 5 TRIFLUOROMETHYLURACIL; 1 (2 DEOXY BETA DEXTRO LYXOFURANOSYL)THYMINE; 1 (2 DEOXY BETA DEXTRO LYXOFURANOSYL)URACIL; 1 (3 DEOXY 3 FLUORO BETA DEXTRO ARABINOFURANOSYL)THYMINE; 1 (3 DEOXY 3 FLUORO BETA DEXTRO ARABINOFURANOSYL)URACIL; 2',3' DIDEOXY 2',3' DIDEHYDRO 2' FLUORO 5 ETHYLURIDINE; 2',3' DIDEOXY 20,30 DIDEHYDRO 20 FLUOROTHYMIDINE; ABACAVIR; ANTIVIRUS AGENT; CLEVUDINE; LAMIVUDINE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG; PYRIMIDINE NUCLEOSIDE;

ANTIBIOTIC RESISTANCE; ANTIVIRAL ACTIVITY; ARTICLE; CHRONIC LIVER DISEASE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DUCK HEPATITIS B; DUCK HEPATITIS B VIRUS; HEPATITIS B; HEPATITIS B VIRUS; HOST CELL; HUMAN; HUMAN CELL; LIVER CELL; VIRUS INHIBITION; VIRUS MUTATION; VIRUS STRAIN; WILD TYPE; ANIMAL; ANTIVIRAL RESISTANCE; CHEMISTRY; DRUG EFFECTS; DUCK; GENETICS; MUTATION; PHYSIOLOGY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE; VIROLOGY; VIRUS REPLICATION;

ANIMALS; ANTIVIRAL AGENTS; CELL LINE, TUMOR; DRUG RESISTANCE, VIRAL; DUCKS; HEPATITIS B VIRUS; HEPATITIS B VIRUS, DUCK; HEPATOCYTES; HUMANS; LAMIVUDINE; MUTATION; PYRIMIDINE NUCLEOSIDES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS REPLICATION;

EID: 77957921826     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100803c     Document Type: Article

References (37)

1. Van Damme, P.; Zanetti, A. R.; Shouval, D.; Herck, K. V. Strategies for Global Prevention of Hepatitis B Virus Infection. In Hot Topics in Infection and Immunity in Children VI; Advances in Experimental Medicine and Biology; Finn, A., Curtis, N., Pollard, A. J., Eds.; Springer: New York, 2010; Vol. 659, pp 175 - 188.
2. Kennedy, M.; Alexopoulos, S. P. Hepatitis B virus infection and liver transplantation Curr. Opin. Organ Transplant. 2010, 15, 310-315
3. Schiller, J. T.; Lowy, D. R. Vaccines to Prevent Infections by Oncoviruses Annu. Rev. Microbiol. 2010, 64, 23-41
4. Kumar, R.; Agrawal, B. Novel Treatment Options for Hepatitis B Virus Infection Curr. Opin. Invest. Drugs 2004, 5, 171-178
5. Cuestas, M. L.; Mathet, V. L.; Oubiúa, J. R.; Sosnik, A. Drug Delivery Systems and Liver Targeting for the Improved Pharmacotherapy of the Hepatitis B Virus (HBV) Infection Pharm. Res. 2010, 27, 1184-1202
6. Villeneuve, J.-P.; Durantel, D.; Durantel, S.; Westland, C.; Xiong, S.; Brosgart, C. L.; Gibbs, C. S.; Parvaz, P.; Werle, B.; Trépo, C.; Zoulim, F. Selection of a hepatitis B virus strain resistant to adefovir in a liver transplantation patient J. Hepatol. 2003, 39, 1085-1089
7. Tillmann, H. L. Antiviral therapy and resistance with hepatitis B virus infection World J. Gastroenterol. 2007, 13, 125-140
8. Agrawal, B.; Srivastav, N. C.; Kumar, R.. Progress in the chemo- and immunotherapeutic interventions for hepatitis B virus In Progress in Hepatitis B Research; Denyer, D. V., Ed.; Nova Science Publishers: New York, 2007; pp 87 - 112.
9. Lange, C. M.; Bojunga, J.; Hofmann, W. P.; Wunder, K.; Mihm, U.; Zeuzem, S.; Sarrazin, C. Severe lactic acidosis during treatment of chronic hepatitis B with entecavir in patients with impaired liver function Hepatology 2009, 50, 2001-2006
10. Matthews, S. J. Telbivudine for the management of chronic hepatitis B virus infection Clin. Ther. 2007, 29, 2635-2653
11. Lui, Y. Y. N.; Chan, H. L. Y. A review of telbivudine for the management of chronic hepatitis B virus infection Expert Opin. Drug Metabol. Toxicol. 2008, 4, 1351-1361
12. Janta-Lipinski, M. V.; Costisella, B.; Ochs, H.; Hübscher, U.; Hafkemeyer, P.; Matthes, E. Newly Synthesized l -Enantiomers of 3′-Fluoro-Modified β-2′-Deoxyribonucleoside 5′-Triphosphates Inhibit Hepatitis B DNA Polymerases But Not the Five Cellular DNA Polymerases α, β, γ, -, and - Nor HIV-1 Reverse Transcriptase J. Med. Chem. 1998, 41, 2040-2046
13. Matthes, E.; Langen, P.; Janta-Lipinski, M. V.; Will, H.; Schröder, H. C.; Merz, H.; Weiler, B. E.; Müller, W. E. Potent inhibition of hepatitis B virus production in vitro by modified pyrimidine nucleosides Antimicrob. Agents Chemother. 1990, 34, 1986-1990
14. Kassianides, C.; Hoofnagle, J. H.; Miller, R. H.; Doo, E.; Ford, H.; Broder, S.; Mitsuya, H. Inhibition of duck hepatitis B virus replication by 2′,3′-dideoxycytidine. A potent inhibitor of reverse transcriptase Gastroenterology 1989, 97, 1275-1280
15. Hui, C. K.; Lau, G. K. Clevudine for the treatment of chronic hepatitis B virus infection Expert Opin. Invest. Drugs 2005, 14, 1277-1284
16. Gupta, S. V.; Tourigny, G.; Stuart, A. L.; De Clercq, E.; Quail, J. W.; Ekiel, I.; El-Kabbani, O. A.L.; Delbaere, L. T. J. Relationship between structure and antiviral activity of 5-methoxymethyl-2′-deoxyuridine and 5-methoxymethyl-1-(2′-deoxy-β- d -lyxofuranosyl)uracil Antiviral Res. 1987, 7, 69-77
17. Veres, Z.; Neszmelyi, A.; Szabolcs, A.; Denes, G. Inhibition of Uridine Phosphorylase by Pyrimidine Nucleoside Analogs and Consideration of Substrate Binding to the Enzyme based on Solution Conformation as seen by NMR Spectroscopy Eur. J. Biochem. 1988, 178, 173-181
18. Welch, J. T. Advances in the Preparation of Biologically Active Organofluorine Compounds Tetrahedron 1987, 43, 3123-3197
19. Gadikota, R. R.; Callam, C. S.; Wagner, T.; Fraino, B. D.; Lowary, T. L. 2,3-Anhydro Sugars in Glycoside Bond Synthesis. Highly Stereoselective Syntheses of Oligosaccharides Containing α-and β -Arabinofuranosyl Linkages J. Am. Chem. Soc. 2003, 125, 4156-4165
20. Lee, B.; Luo, W.; Suzuki, S.; Robins, M. J.; Tyrrell, D. L. J. In Vitro and in Vivo Comparison of the Abilities of Purine and Pyrimidine 2′,3′-Dideoxynucleosides to Inhibit Duck Hepadnavirus Antimicrob. Agents Chemother. 1989, 33, 336-339
21. Tuttleman, J. S.; Pugh, J. C.; Summers, J. W. In Vitro Experimental Infection of Primary Duck Hepatocyte Cultures with Duck Hepatitis B Virus J. Virol. 1986, 58, 17-25
22. Walters, K. A.; Tipples, G. A.; Allen, M. I.; Condreay, L. D.; Addison, W. R.; Tyrrell, L. Generation of Stable Cell Lines Expressing Lamivudine-Resistant Hepatitis B Virus for Antiviral-Compound Screening Antimicrob. Agents Chemother. 2003, 47, 1936-1942
23. Palomino, E.; Meltsner, B. R.; Kessel, D.; Horwitz, J. P. Synthesis and in Vitro Evaluation of Some Modified 4-Thiopyrimidine Nucleosides for Prevention or Reversal of AIDS-Associated Neurological Disorders J. Med. Chem. 1990, 33, 258-263
24. Martin, J. A.; Bushnell, D. J.; Duncan, I. B.; Dunsdon, S. J.; Hall, M. J.; Machin, P. J.; Merrett, J. H.; Parkes, K. E. B.; Roberts, N. A. Synthesis and antiviral activity of monofluoro and difluoro analogs of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1) J. Med. Chem. 1990, 33, 2137-2145
25. Czernecki, S.; Diguarher, T. Le.; Valery, J. M. Synthesis and Anti-HIV Activity of Base Modified Analogues of 3′-Azido-2′,3′- dideoxythymidine (AZT) Nucleosides Nucleotides 1993, 12, 369-380
26. Chou, T.-C.; Kong, X.-B.; Fanucchi, M. P.; Cheng, Y.-C.; Takahashi, K.; Watanabe, K. A.; Fox, J. J. Synthesis and Biological Effects of 2′-Fluoro-5-ethyl-1-β- d -arabinofuranosyluracil Antimicrob. Agents Chemother. 1987, 31, 1355-1358
27. Chu, C. K.; Schinazi, R. F.; Ahn, M. K.; Ullas, G. V.; Gu, Z. P. Structure-Activity Relationships of Pyrimidine Nucleosides as Antiviral Agents for Human Immunodeficiency Virus Type 1 in Peripheral Blood Mononuclear Cells J. Med. Chem. 1989, 32, 612-617
28. Fox, J. J.; Miller, N. C. Nucleosides. XVI. Further Studies of Anhydronucleosides J. Org. Chem. 1963, 28, 936-941
29. Johar, M.; Manning, T.; Kunimoto, D. Y.; Kumar, R. Synthesis and in Vitro Antimycobacterial Activity of 5-Substituted Pyrimidine Nucleosides Bioorg. Med. Chem. 2005, 13, 6663-6671
30. Agyei-aye, K.; Yan, S.; Hebbler, A. K.; Baker, D. C. Preparation of 2,3′-Anhydropyrimidine Nucleosides using N, N -Diethylaminosulfur Trifluoride (DAST) Nucleosides Nucleotides 1989, 8, 327-337
31. McGuigan, C.; Carangio, A.; Snoeck, R.; Andrei, G.; Clercq, E. D.; Balzarini, J. Synthesis and Antiviral Evaluations of Some 3′-Fluoro Bicyclic Nucleoside Analogues Nucleosides, Nucleotides Nucleic Acids 2004, 23, 1-5
32. Ashwell, M.; Jones, A. S.; Walker, R. T. The Synthesis of Some Branched-Chain-Sugar Nucleoside Analogues Nucleic Acids Res. 1987, 15, 2157-2166
33. Huang, J.-T.; Chen, L.-C.; Wang, L.; Kim, M.-H.; Warshaw, J. A.; Armstrong, D.; Zhu, Q.-Y.; Chou, T.-C.; Watanabe, K. A.; Matulic-Adamic, J.; Su, T.-L.; Fox, J. J.; Polsky, B.; Baron, P. A.; Gold, J. W. M.; Hardy, W. D.; Zuckerman, E. Fluorinated Sugar Analogues of Potential Anti-HIV-1 Nucleosides J. Med. Chem. 1991, 34, 1640-1646
34. Cushley, R. J.; Codington, J. F.; Fox, J. J. Nucleosides. XLIX. Nuclear magnetic resonance studies of 2′-and 3′-halogeno nucleosides. The conformations of 2′-deoxy-2′-fluorouridine and 3′-deoxy- 3′-fluoro-β- d -arabinofuranosyluracil Can. J. Chem. 1968, 46, 1131-1140
35. Kumar, R.; Semaine, W.; Johar, M.; Tyrrell, D. L. J.; Agrawal, B. Effect of Various Pyrimidines Possessing the 1-[(2-Hydroxy-1-(hydroxymethyl)ethoxy) methyl] Moiety, Able To Mimic Natural 2′-Deoxyribose, on Wild-type and Mutant Hepatitis B Virus Replication J. Med. Chem. 2006, 49, 3693-3700
36. Sells, M. A.; Chen, M. L.; Acs, M. L. Production of Hepatitis B Virus Particles in Hep G2 Cells Transfected with Cloned Hepatitis B Virus DNA Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 1005-1009
37. Korba, B. E.; Boyd, M. R. Penciclovir is a Selective Inhibitor of Hepatitis B Virus Replication in Cultured Human Hepatoblastoma Cells Antimicrob. Agents Chemother. 1996, 40, 1282-1284