Synthesis and antiviral activity evaluation of acyclic 2′-azanucleosides bearing a phosphonomethoxy function in the side chain

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 11, 2009, Pages 3756-3762

  Koszytkowska Stawińska, Mariola ^a   Clercq, Erik De ^b   Balzarini, Jan ^b  

^a WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Acyclic nucleoside phosphonates; Antiviral agents; Azanucleosides; Nucleoside analogs; Sulfonamides

Indexed keywords

[2 [N (1H,3H PYRIMIDIN 2,4 DION 1 YLMETHYL) N (4 TOLUENESULFONYL)AMINO]ETHOXYMETHYL]PHOSPHONIC ACID; [2 [N (5 FLUORO 1H,3H PYRIMIDIN 2,4 DION 1 YLMETHYL) N (4 TOLUENESULFONYL)AMINO]ETHOXYMETHYL]PHOSPHONIC ACID; [2 [N (5 METHYL 1H,3H PYRIMIDIN 2,4 DION 1 YLMETHYL) N (4 TOLUENESULFONYL)AMINO]ETHOXYMETHYL]PHOSPHONIC ACID; ACYCLIC NUCLEOSIDE; ADEFOVIR; CIDOFOVIR; DIETHYL [2 [N (PIVALOYLOXYMETHYL) N (4 TOLUENESULFONYL)AMINO]ETHOXYMETHYL]PHOSPHONIC ACID; PHOSPHONIC ACID DERIVATIVE; TENOFOVIR; UNCLASSIFIED DRUG;

ACYLATION; ALKYLATION; ANTIVIRAL ACTIVITY; ARTICLE; DNA VIRUS; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NONHUMAN; RNA VIRUS;

ACIDS, ACYCLIC; ADENINE; ANTIVIRAL AGENTS; AZA COMPOUNDS; CYTOSINE; DNA VIRUSES; HELA CELLS; HUMANS; MOLECULAR STRUCTURE; NUCLEOSIDES; PHOSPHONIC ACIDS; RNA VIRUSES;

DNA VIRUSES;

EID: 65549171019     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.04.054     Document Type: Article

References (31)

1. De Clercq E. J. Clin. Virol. 30 (2004) 115
2. Holý A. Curr. Pharm. Des. 9 (2003) 2567
3. De Clercq E., and Holý A. Nat. Rev. Drug Discovery 4 (2005) 928
4. For the selected papers on the ANP analogues with modifications in acyclic moiety, see:. Jeffery A.L., Kim J.-H., and Wiemer D.F. Tetrahedron 56 (2000) 5077
5. Esteban-Gamboa A., Balzarini J., Esnouf R., De Clercq E., Camarasa J.-M., and Pérez-Pérez M.-J. J. Med. Chem. 43 (2000) 971
6. Rejman D., Masojidkova M., De Clercq E., and Rosenberg I. Nucleosides Nucleotides 20 (2001) 1497
7. Choi J.-R., Cho D.-G., Roh K.Y., Hwang J.-T., Ahn S., Jang H.S., Cho W.-Y., Kim, K W., Cho Y.-G., Kim J., and Kim Y.-Z. J. Med. Chem. 47 (2004) 2864
8. Kim A., and Hong J.H. Arch. Pharm. (Weinheim, Ger.) 338 (2005) 528
9. Wu M., El-Kattan Y., Lin T.-H., Ghosh A., Kumar V.S., Kotian P.L., Cheng X., Bantia S., Babu Y.S., and Chand P. Nucleosides Nucleotides 24 (2005) 1569
10. Ivanov A.V., Andronova V.L., Galegov G.A., and Jasko M.V. Russ. J. Bioorg. Chem. 31 (2005) 58 (Bioorg. Khim. 2005, 31, 65)
11. Oh C.H., and Hong J.H. Arch. Pharm. 339 (2006) 507
12. Pomeisl K., Votruba I., Holý A., and Pohl R. Collect. Czech. Chem. Commun. 71 (2006) 595
13. Kim A., and Hong J.H. Nucleosides Nucleotides 25 (2006) 1399
14. Vrobska S., Holý A., Pohl R., and Masojidkova M. Collect. Czech. Chem. Commun. 71 (2006) 543
15. Kim A., and Hong J.H. Nucleosides Nucleotides 25 (2006) 941
16. Pham P.-T., and Vince R. Phosphorus, Sulfur Silicon Relat. Elem. 182 (2007) 779
17. Vrbkova S., Dracínsky M., and Holý A. Tetrahedron: Asymmetry 18 (2007) 2233
18. Zhou D., Lagoja I.M., Van Aerschot A., and Herdewijn P. Collect. Czech. Chem. Commun. 71 (2006) 15
19. Harnden M.R., and Jarvest R.L. Bioorg. Med. Chem. Lett. 2 (1992) 1559
20. Vaněk V., Buděšinský M., Rinnová M., and Rosenberg I. Tetrahedron 65 (2009) 862
21. Koszytkowska-Stawińska M., and Sas W. Tetrahedron Lett. 45 (2004) 5437
22. Koszytkowska-Stawińska M., Sas W., and De Clercq E. Tetrahedron 62 (2006) 10325
23. Koszytkowska-Stawińska M., Kaleta K., Sas W., and De Clercq E. Nucleosides Nucleotides 26 (2007) 51
24. Koszytkowska-Stawińska M., Kołaczkowska E., Adamkiewicz E., and De Clercq E. Tetrahedron 63 (2007) 10587
25. Gawin R., De Clercq E., Naesens L., and Koszytkowska-Stawińska M. Bioorg. Med. Chem. 16 (2008) 8379
26. Bronson J.J., Ghazzouli I., Hitchcock M.J.M., Webb R.R., and Martin J.C. J. Med. Chem. 32 (1989) 1457
27. The preparation of 9 in 68% yield form diethyl (2-chloroethoxy)methylphosphonate and sodium azide under phase transfer catalysis conditions at 90 °C was also reported:. Eger K., Kluender E., and Schmidt M. J. Med. Chem. 37 (1994) 3057
28. Martin A.E., Ford T.M., and Bulkowski J.E. J. Org. Chem. 47 (1982) 412
29. Vrbková S., Dracínský M., and Holý A. Tetrahedron 63 (2007) 11391
30. Khandazhinskaya A., Yasko M., and Shirokova E. Curr. Med. Chem. 13 (2006) 2953
31. Starrett Jr. J.E., Tortolani D.R., Russell J., Hitchcock M.J.M., Whiterock V., Martin J.C., and Mansuri M.M. J. Med. Chem. 37 (1994) 1857