Synthesis and biological evaluation of phosphonated dihydroisoxazole nucleosides

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 11, 2006, Pages 3818-3824

  Romeo, Giovanni ^a   Iannazzo, Daniela ^a   Piperno, Anna ^a   Romeo, Roberto ^a   Saglimbeni, Monica ^a   Chiacchio, Maria Assunta ^b   Balestrieri, Emanuela ^c   Macchi, Beatrice ^c   Mastino, Antonio ^a  

^a UNIVERSITY OF MESSINA   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

^c UNIVERSITY OF ROME TOR VERGATA   (Italy)

Author keywords

1,3 Dipolar cycloaddition; Antiviral agents; Isoxazoline nucleotides; Phosphonated nucleosides

Indexed keywords

[5 (4 ACETYLAMINO 2 OXO 2H PYRIMIDIN 1 YL) 4,5 DIHYDROISOXAZOL 3 YLMETHYL]PHOSPHONIC ACID DIETHYL ESTER; [5 (4 ACETYLAMINO 2 OXO 2H PYRIMIDIN 1 YLMETHYL) 4,5 DIHYDROISOXAZOL 3 YLMETHYL]PHOSPHONIC ACID DIETHYL ESTER; ACICLOVIR; ANTIVIRUS AGENT; DIETHYL [1 [[(5 METHYL 2,4 DIOXO 3,4 DIHYDROPYRIMIDIN 1(2H) YL]] 3' METHYL 2' OXA 3' AZACYCLOPENT 4' YL]METHYLPHOSPHONATE; DIETHYL [4,4 DIHYDRO 5 (3,4 DIHYDRO 5 METHYL 2,4 DIOXOPYRIMIDIN 1(2H) YL)ISOXAZOL 3 YL]METHYLPHOSPHONATE; DIETHYL [4,5 DIHYDRO 5 (3,4 DIHYDRO 5 METHYL 2,4 DIOXOPYRIMIDIN 1(2H) YL)METHYLISOXAZOL 3 YL]METHYLPHOSPHONATE; DIETHYL [5 (5 FLUORO 3,4 DIHYDRO 2,4 DIOXOPYRIMIDIN 1(2H) YL) 4,5 DIHYDROISOXAZOL 3 YL]METHYLPHOSPHONATE; DIETHYL [5 (5 FLUORO 3,4 DIHYDRO 2,4 DIOXOPYRIMIDIN 1(2H) YLMETHYL) 4,5 DIHYDROISOXAZOL 3 YL]METHYLPHOSPHONATE; NITRILE OXIDE; NUCLEOSIDE ANALOG; RNA DIRECTED DNA POLYMERASE; UNCLASSIFIED DRUG; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYCLOADDITION; CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; NONHUMAN; RETROVIRUS;

ANIMALS; ANTIVIRAL AGENTS; AVIAN MYELOBLASTOSIS VIRUS; CELL LINE, TUMOR; CELL PROLIFERATION; CELLS, CULTURED; CERCOPITHECUS AETHIOPS; CYCLIZATION; HERPESVIRUS 1, HUMAN; HUMANS; ISOXAZOLES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; NUCLEOSIDES; PHOSPHONIC ACIDS; REVERSE TRANSCRIPTASE INHIBITORS; RNA-DIRECTED DNA POLYMERASE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS;

HUMAN HERPESVIRUS 1; HUMAN HERPESVIRUS 2;

EID: 33646071200     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.01.028     Document Type: Article

References (45)

1. De Clercq E. J. Med. Chem. 48 (2005) 1-16
2. Qiu X.L., and Qing F.L. Bioorg. Med. Chem. 13 (2005) 277-283
3. Chen X., Zhou W., Schinazi R.F., and Chu C.K. J. Org. Chem. 69 (2004) 6034-6041
4. Siddiqui M.A., Hughes S.H., Boyer P.L., Mitsuya H., Van Q.N., George C., Sarafinanos S.G., and Marquez V.E.A. J. Med. Chem. 47 (2004) 5041-5048;
5. Ferrero M., and Gotor V. Chem. Rev. 100 (2000) 4319-4347
6. Chu C.K., and Baker D.C. Nucleosides and Nucleotides as Antitumor and Antiviral Agents (1993), Plenum Press, New York
7. Chong Y., Gumina G., and Chu C.K. Tetrahedron: Asymmetry 11 (2000) 4853-4875
8. Freeman S., and Gardiner J.M. Mol. Biotechnol. 5 (1996) 125-137
9. Chen J., Sambaiah T., Illarionov B., Fischer M., Bacher A., and Cushman M. J. Org. Chem. 69 (2004) 6996-7003
10. Hakimelahi, G. H. U.S. Patent Appl., 2004, CODEN: USXXCO US 2004002475 A1 20040101 CAN 140:59903.
11. Amblard F., Aucagne V., Guenot P., Schinazi R.F., and Agrofoglio L.A. Bioorg. Med. Chem. 13 (2005) 1239-1248
12. Rodriguez J.B., and Comin M.J. Mini-Rev. Med. Chem. 3 (2003) 95-114
13. Ichikawa E., and Kato K. Curr. Med. Chem. 8 (2001) 385-423
14. Merino P. Curr. Med. Chem: Anti-infective Agents 1 (2002) 389-411
15. Tronquet J.M., Zscly M., Cock K., and De Villedam de Naide F. Bioorg. Med. Chem. Lett. 2 (1992) 1723-1728
16. Chiacchio U., Corsaro A., Iannazzo D., Piperno A., Pistarà V., Rescifina A., Romeo R., Sindona G., and Romeo G. Tetrahedron: Asymmetry 14 (2003) 2717-2723
17. Chiacchio U., Borrello L., Iannazzo D., Merino P., Piperno A., Rescifina A., Richichi B., and Romeo G. Tetrahedron: Asymmetry 14 (2003) 2419-2425
18. Chiacchio U., Corsaro A., Rescifina A., Romeo G., and Romeo R. Tetrahedron: Asymmetry 11 (2000) 2045-2048
19. Chiacchio U., Corsaro A., Iannazzo D., Piperno A., Pistarà V., Rescifina A., Romeo R., Valveri V., Mastino A., and Romeo G. J. Med. Chem. 46 (2003) 3696-3702
20. Gi H.J., Kiang Y., Schinazi R.F., and Zhao K. J. Org. Chem. 62 (1997) 88-92
21. Xiang Y., Chen J., Schinazi R.F., and Zhao K. Bioorg. Med. Chem. Lett. 6 (1996) 1051-1054
22. Johansson N.G., and Eriksson S. Acta Biochim. Pol. 43 (1996) 143-160
23. Wagner C.R., Iyer V.V., and McIntee E.J. Med. Res. Rev. 20 (2000) 417-451
24. Shirokowa E.A., Jasko M.V., Khandazhinskaya A.L., Ivanov A.V., Yanvarev D.V., Skoblov Y.S., Mitkevitch V.A., Bocharov E.V., Pronyaeva T.R., Fedyuk N.V., Kukhanova M.K., and Pokrovsky A.G. J. Med. Chem. 47 (2004) 3606-3614
25. Balzarini J., Holy A., Jindrich J., Naesens L., Snoeck R., Schols D., and De Clercq E. Antimicrob. Agents Chemother. 37 (1993) 332-338
26. Chiacchio U., Balestrieri E., Macchi B., Iannazzo D., Piperno A., Rescifina A., Romeo R., Saglimbeni M., Sciortino M.T., Valveri V., Mastino A., and Romeo G. J. Med. Chem. 48 (2005) 1389-1394
27. Guan H.P., Qiu Y.L., Ksebati M.B., Kern E.R., and Zemlicka J. Tetrahedron 58 (2002) 6047-6059
28. Holy A., De Clerq E., and Votruba I. In: Martin J.C. (Ed). Nucleotide Analogues as Antiviral Agents (1989), American Chemical Society, Washington, DC 55-71
29. Harnden M.R., Parkin A., Parrot M.J., and Perkins R.M. J. Med. Chem. 36 (1993) 1343-1355
30. Nguyen-Ba P., Turcotte N., Yuen L., Berdart J., Quimpere M., and Chan L. Bioorg. Chem. Med. Lett. 8 (1998) 3561-3566
31. Serafinowska H.T., Ashton R.J., Bailey S., Harnden M.R., Jackson S.M., and Sutton D.J. J. Med. Chem. 38 (1995) 1372-1379
32. Kim C.U., Luh B.Y., and Martin J.C. J. Org. Chem. 56 (1991) 2642-2647
33. Tsuge O., Kanemasa S., Suca H., and Nakacawa N. Bull. Chem. Soc. Jpn. 60 (1987) 2463-2473
34. Dalpozzo R., De Nino A., Maiuolo L., Procopio A., Romeo R., and Sindona G. Synthesis 2 (2002) 172-174
35. Adams D.R., Boyd A.S.F., and Ferguson R. Nucleosides Nucleotides 17 (1998) 1053-1074
36. Chiacchio U., Corsaro A., Iannazzo D., Piperno A., Ristarà V., Procopio A., Rescifina A., Romeo G., Romeo R., Siciliano M.C.R., and Valveri E. Arkivoc (2002) 159-167
37. De Amici M., De Micheli C., and Misani V. Tetrahedron 46 (1990) 1975-1986
38. De Amici M., Magri P., De Micheli C., Cateni F., Bovara R., Carrea G., Riva S., and Canalone G. J. Org. Chem. 57 (1992) 2825-2829
39. Bacher E., Demnitz F.W.J., and Hurni T. Tetrahedron 53 (1997) 14317-14326
40. Marquez V.E., Ezzitouni A., Russ P., Siddiqui M.A., Ford H., Feldman R., Mitsuya H., George C., and Barchi. J. Am. Chem. Soc. 120 (1998) 2780-2789
41. Lamberth C. Org. Prep. Proc. Int. 34 (2002) 149-167
42. Chiacchio U., Genovese F., Iannazzo D., Librando V., Merino P., Rescifina A., Romeo R., Procopio A., and Romeo G. Tetrahedron 60 (2004) 441-448
43. Nkusi G., and Neidlein R. Journal fuer praktische Chemie/Chemiker-Zeitung 334 (1992) 278-280
44. Coutouli-Argyropoulou E., and Pilanidou P. Tetrahedron Lett. 44 (2003) 3755-3758
45. Sigel H. Chem. Soc. Rev. 33 (2004) 191-200