Skip to main content
Log in

RETRACTED ARTICLE: Synthesis and biological evaluation of entecavir 4′-ester derivatives

  • Published:
Chemical Research in Chinese Universities Aims and scope

This article was retracted on 22 December 2015

Abstract

Entecavir can significantly inhibit the replication of HBV-DNA, reduce the HBV-DNA level in blood serum. But suffering from low oral bioavailability, entecavir has low intestinal membrane permeability and poor metabolic stability. In this study, 12 different derivatives of entecavir 4′-ester were regioselectively synthesized and their apical-to-basolateral permeabilities across Caco-2 cells and HBV-DNA inhibitory efficacies were evaluated. Most of the compounds showed high permeabilities across Caco-2 cells compared with entecavir, compounds 5b and 5e also exhibited comparable anti-HBV activities with that of entecavir, especially.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Shi C. C., Tjwa E. T., Biesta P. J., Boonstra A., Xie Q., Janssen H. L., Woltman A. M., J. Vir. Hepatitis, 2012, 19(2), 26

    Article  CAS  Google Scholar 

  2. Pothakamuri V. S., Sven P., Verena S., Jan G., Paraskevi F., Anna G., Birgit B.B., Antoaneta M., Jerzy J., Christoph B., Michael P. M., Markus C., Heiner W., Hepatology, 2012, 55(3), 695

    Article  CAS  Google Scholar 

  3. Jensbukh M. D., Robert E., Lanford P. D., Robert H., Purcell M. D., Hepatology, 2013, 58(5), 1533

    Article  Google Scholar 

  4. Rehermann B., Nascimbeni M., Nat. Rev. Immunol., 2005, 5(3), 215

    Article  CAS  Google Scholar 

  5. Fisicaro P., Valdatta C., Boni C., Massari M., Mori C., Zerbini C., Orlandini A., Sacchelli L., Missale G., Ferrari C., Hepatology, 2009, 58, 974

    CAS  Google Scholar 

  6. Daniel G., Maximilian H., Robert T., Clin. Sci., 2013, 124, 77

    Article  CAS  Google Scholar 

  7. Han Q. J., Zhang C., Zhang J., Tian Z. G., Semin. Immunopathol, 2013, 35(1), 23

    Article  CAS  Google Scholar 

  8. Dienstag J. L., Perrillo R. P., Schiff E. R., Bartholomew M., Vicary C., Rubin M., N. Engl. J. Med., 1995, 333, 1657

    Article  CAS  Google Scholar 

  9. Cullen J. M., Li D. H., Brown C., Eisenberg E. J., Cundy K. C., Wolfe J., Toole J., Gibbs C., Antimicrob. Agents Chemother., 2001, 45(10), 2740

    Article  CAS  Google Scholar 

  10. Stevens R. C., Blum M. R., Rousseau F. S., Kearney B. P., Anderson P. L., Kakuda T. N., Lichtenstein K. A., Clin. Infect. Dis., 2004, 39, 877

    Article  Google Scholar 

  11. Marcellin P., Mommeja M. H., Sacks S. L., Lau G. K., Sereni D., Bronowicki J. P., Conway B., Trepo C., Blum M. R., Yoo B. C., Mondou E., Sorbel J., Snow A., Rousseau F., Lee H. S., Hepatology, 2004, 40, 140

    Article  CAS  Google Scholar 

  12. Chu C. K., Ma L., Olgen S., Pierra C., Du J., Gumina G., Gullen E., Cheng Y. C., Schinazi R. F., J. Med. Chem., 2000, 43(21), 3906

    Article  CAS  Google Scholar 

  13. Honkoop P., Deman R. A., Opin. Investig. Drugs, 2003, 12(4), 683

    Article  CAS  Google Scholar 

  14. Tenney D. J., Levine S. M., Rose R. E., Walsh A. W., Weinheimer S. P., Discotto L., Plym M., Pokornowski K., Yu C. F., Angus P., Ayres A., Bartholomeusz A., Sievert W., Thompson G., Warner N., Locarnini S., Colonno R. J., Antimicrob. Agents Chemother., 2004, 48(9), 3498

    Article  CAS  Google Scholar 

  15. Innaimo S. F., Seifer M., Bisacchi G. S., Standring D. N., Zahler R., Colonno R. J., Antimicrob. Agents. Chemoter., 1997, 41, 1444

    CAS  Google Scholar 

  16. Buti M., Esteban R., J. Hepatol., 2003, 39(2), 239

    Article  Google Scholar 

  17. Benjahad A., CouRte K., Guillemont J., Mabire D., Coupa S., Poncelet A., Csoka I., Andries K., Pauwels R., de Bethune M. P., Monneret C., Bisagni E., Nguyen C. H., Grierson D. S., J. Med. Chem., 2004, 47(22), 5501

    Article  CAS  Google Scholar 

  18. Lv Z., Sheng C., Wang T., J. Med. Chem., 2010, 53(18), 6600

    Google Scholar 

  19. Sun Y. B., Sun J., Shi S. L., Jing Y. K., Yin S. L., Chen Y., Li G., Xu Y. J., He Z. G., Mol. Pharmaceutics, 2009, 6(1), 315

    Article  CAS  Google Scholar 

  20. Yan Z. T., Sun J., Chang Y. N., Liu Y. H., Fu Q., Xu Y. J., Sun Y. B., Pu X. H., Zhang Y. X., Jing Y. K., Yin S. L., Zhu M., Wang Y. J., He Z. G., Mol. Pharmaceutics, 2011, 8(2), 319

    Article  CAS  Google Scholar 

  21. Balimane P. V., Tamai I., Guo A. L., Nakanishi T., Kitada H., Leibach F. H., Tsuji A., Sinko P. J., Biochem. Biophys. Res. Commun., 1998, 250, 246

    Article  CAS  Google Scholar 

  22. Bueno A. B., Collado I., de Dios A., Domingguez C., Martin J. A., Martin L. M., Matinez-Grau M. A., Montero C., Pedregal C., Catlow J., Coffey D. S., Cley M.P., Dantzig A. H., Lindstrom T., Monn J. A., Jiang H. Y., Schoepp D. D., Stratford R. E., Tabas L. B., Tizaano J. P., Wright R. A., Herin M. F., J. Med. Chem., 2005, 48(16), 5305

    Article  CAS  Google Scholar 

  23. Zhang Y. X., Sun J., Gao Y. K., Jin L., Xu Y. J., Lian H., Sun Y. B., Sun Y. H., Liu J. Y., Fan R., Zhang T. H., He Z. G., Mol. Pharmaceutics, 2013, 10(8), 3195

    Article  CAS  Google Scholar 

  24. Perkins E. J., Abraham T., Drug Metab. Dispos., 2007, 35(10), 1903

    Article  CAS  Google Scholar 

  25. Gregory Y., Todd W., Steven I., Gregory S. B., Peter E., Kent R., Robert Z., Richard J. C., Antimicrob. Agents Chemother., 1999, 43(1), 190

    Google Scholar 

  26. Liu Y., Lu B. W., Lu J. R., Xin C. W., Li J. F., Mu J. B., Bao X. R., Chem. Res. Chinese Universities, 2013, 29(3), 449

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Youjun Xu.

Additional information

Supported by the National Natural Science Foundation of China(No.51209024) and the Science and Technology Plan of Sichuan Province, China(No.2010JY0122).

This article is retracted because the corresponding author XU Youjun was put as the corresponding author without knowing anything before its publication. All were arranged by the first author, Mr. FENG Deri, in abnormal ways. Hence all other authors and XU states here that this paper has no relation with other authors and with Xu’s working university. XU also states that he has never used “xuyoujun65@163.com”as corresponding author contact email. Therefore XU declares that the paper should be withdrawn from the journal as soon as possible in case any negative effects on other authors and on this journal.

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Feng, D., Liu, J., Liang, S. et al. RETRACTED ARTICLE: Synthesis and biological evaluation of entecavir 4′-ester derivatives. Chem. Res. Chin. Univ. 30, 749–754 (2014). https://doi.org/10.1007/s40242-014-4183-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40242-014-4183-y

Keywords

Navigation