Design, synthesis and evaluation of novel oxazaphosphorine prodrugs of 9-(2-phosphonomethoxyethyl)adenine (PMEA, adefovir) as potent HBV inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 24, 2009, Pages 6918-6921

  Lu, Peng ^a   Liu, Jiangxia ^b   Wang, Yuya ^a   Chen, Xiaoyan ^a   Yang, Yushe ^a   Ji, Ruyun ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

^b FUDAN UNIVERSITY   (China)

Author keywords

Hepatitis B virus; Oxazaphosphorine; Prodrug

Indexed keywords

ADEFOVIR DIPIVOXIL; OXAZAPHOSPHORINE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; CELL ASSAY; CELL STRAIN HEPG2; CONTROLLED STUDY; DIASTEREOISOMER; DRUG DESIGN; DRUG METABOLISM; DRUG POTENCY; DRUG RELEASE; DRUG STABILITY; DRUG SYNTHESIS; EVALUATION; HEPATITIS B VIRUS; HUMAN; HUMAN CELL; IC 50; LIVER MICROSOME;

ADENINE; ANTIVIRAL AGENTS; CELL LINE, TUMOR; DRUG DESIGN; HEPATITIS B VIRUS; HUMANS; ORGANOPHOSPHORUS COMPOUNDS; PHOSPHONIC ACIDS; PRODRUGS;

HEPATITIS B VIRUS;

EID: 71949122979     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.10.072     Document Type: Article

References (32)

1. Malik A., and Lee W. Ann. Intern. Med. 132 (2000) 723
2. Wong D.K.H., Cheung A.M., O'Rourke K., Naylor C.D., Detsky A.S., and Heathcote J. Ann. Intern. Med. 119 (1993) 312
3. Lok A.S., Hussain M., Cursano C., Margotti M., Gramenzi A., Grazi G.L., Jovine E., Benardi M., and Andreone P. Hepatology 32 (2000) 1145
4. Kim J.W., Park S.H., and Louie S.G. Ann. Pharmacother. 40 (2006) 472
5. De Clercq E., Sakuma T., Baba M., Pauwels R., Balzarini J., Rosenberg I., and Holy A. Antiviral Res. 8 (1987) 261
6. Yokota T., Mochizuki S., Konno K., Mori S., Shigheta S., and De Clercq E. Antimicrob. Agents Chemother. 35 (1991) 394
7. Ulrika E., John M.H., Jae-Seung K., Stefanie M., Paul K., Katherine Z.B., Julie M.B., John C.D., Boris A.K., and Charles E.M. Bioorg. Med. Chem. Lett. 17 (2007) 583
8. Krise J.P., and Stella V.J. Adv. Drug Delivery Rev. 19 (1996) 287
9. Schultz C. Bioorg. Med. Chem. 11 (2003) 885
10. Chen Z., and Zheng M. Exp. Opin. Ther. Patents 15 (2005) 1027
11. Douglas H.S., Kevin T.B., and Sanjay K.N. Am. J. Physiol. Renal Physiol. 281 (2001) F197
12. Speit G., Schutz P., and Merk O. Mutagenesis 15 (2000) 85
13. Lefebvre I., Perigaud C., Pompon A., Aubertin A.M., Girarder J.L., Kirn A., Gosselin G., and Imbach J.L. J. Med. Chem. 38 (1995) 3941
14. McGuigan C., Pathirana R.N., Balzarini J., and De Clercq E. J. Med. Chem. 36 (1993) 1048
15. Sorensen M.D., Blæhr L.K.A., Christensen M.K., Hoyer T., Latini S., Hjarnaa P.V., and Björkling F. Bioorg. Med. Chem. 11 (2003) 5461
16. Erion M.D., Reddy K.R., Boyer S.H., Matelich M.C., Gomez-Galeno J., Lemus R.H., Ugarkar B.G., Colby T.J., Schanzer J., and Van Poelje P.D. J. Am. Chem. Soc. 126 (2004) 5154
17. Erion M.D., Van Poelje P.D., Mackenna D.A., Colby T.J., Montag A.C., Fujitaki J.M., Linemeyer D.L., and Bullough D.A. J. Pharmacol. Exp. Ther. 46 (2005) 4321
18. Hecker S.J., Reddy R., Van Poelje P.D., Sun Z., Varkhedkar W., Huang V., Reddy M.V., Fujitaki J.M., Olsen D.B., Koeplinger K.A., Boyer S.H., MacCoss D.L., Linemeyer M., and Erion M.D. J. Med. Chem. 50 (2007) 3891
19. 3).
20. Pikul S., Dunham K.L.M., Almstead N.G., De B., Natchus M.G., Anastasio M.V., McPhail S.J., Snider C.E., Taiwo Y.O., Chem L., Dunaway C.M., Gu F., and Mieling G.E. J. Med. Chem. 42 (1999) 87
21. Sawa M., Kiyoi T., Kurokawa K., Kumihara H., Yamamoto M., Miyasaka T., Ito Y., Hirayama R., Inoue T., Kirii Y., Nishiwaki E., Ohmoto H., Maeda Y., Ishibushi E., Inoue Y., Yoshino K., and Kondo H. J. Med. Chem. 45 (2002) 919
22. Mosbo J., and Verkade J.G.A. J. Org. Chem. 42 (1977) 1549
23. Cooper D.B., Harrison J.M., Inch T.D., and Lewis G.J. J. Chem. Soc., Perkin Trans. 1 (1974) 1049
24. Mary A.S., Cheng M.L., and George A. Proc. Natl. Acad. Sci. U.S.A. 84 (1987) 1005
25. Fu X.Z., Jiang S.H., Li C., Xin J., Yang Y.S., and Ji R.Y. Bioorg. Med. Chem. Lett. 17 (2007) 465
26. Farquhar D., Srivastva D.N., Kattesch N.J., and Saunders P.P. J. Pharm. Sci. 72 (1983) 324
27. Farquhar D., Khan S., Srivastva D.N., and Saunder P.P. J. Med. Chem. 37 (1994) 3902
28. Dang Q., Brown B.S., van Poelje P.D., Colby T.C., and Erion M.D. Bioorg. Med. Chem. Lett. 9 (1999) 1505
29. Banijamali A.R., Xu Y., Dematteo V., Strunk R.J., and Sumner S.J. J. Agric. Food. Chem. 48 (2000) 4693
30. Balzarini J., Hao Z., Herdewjin P., Johns D., and De Clercq E. Proc. Natl. Acad. Sci. U.S.A. 88 (1991) 1499
31. Merta A., and Votruba I. J. Biochem. Pharmacol. 44 (1992) 2067
32. Robbins B., Greenhaw J., Connelly M., and Fridland A. Antimicrob. Agents Chemother. 39 (1995) 2304