Prolinol-based nucleoside phosphonic acids: new isosteric conformationally flexible nucleotide analogues

Tetrahedron

Volumn 65, Issue 4, 2009, Pages 862-876

  Vaněk, Václav ^a   Buděšínský, Miloš ^a   Rinnová, Markéta ^a   Rosenberg, Ivan ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Inversion of configuration; N Alkylation; Nucleotide analogues; Phosphonates; Prolinol derivatives

Indexed keywords

1 (2,6 DIAMINOPURIN 9 YL) 1,2,3 TRIDEOXY 3 AZA 4A CARBA ALPHA LEVO GLYCERO PENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; 1 (2,6 DIAMINOPURIN 9 YL) 1,2,3 TRIDEOXY 3 AZA 4A CARBA BETA LEVO GLYCERO PENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; 1 (ADENIN 9 YL) 1,2,3 TRIDEOXY 3 AZA 4A CARBA ALPHA LEVO GLYCEROPENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; 1 (ADENIN 9 YL) 1,2,3 TRIDEOXY 3 AZA 4A CARBA BETA LEVO GLYCEROPENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; 1 (CYTOSIN 1 YL) 1,2,3 TRIDEOXY 3 AZA 4A CARBA ALPHA LEVO GLYCEROPENTOFURANOS; 1 (CYTOSIN 1 YL) 1,2,3 TRIDEOXY 3 AZA 4A CARBA BETA LEVO GLYCEROPENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; 1 (GUANIN 9 YL) 1,2,3 TRIDEOXY 3 AZA 4A CARBA ALPHA LEVO GLYCEROPENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; 1 (GUANIN 9 YL) 1,2,3 TRIDEOXY 3 AZA 4A CARBA BETA LEVO GLYCEROPENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; 1 (THYMIN 1 YL) 1,2,3 TRIDEOXY 3 AZA 4A CARBA ALPHA LEVO GLYCEROPENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; 1 (THYMIN 1 YL) 1,2,3 TRIEOXY 3 AZA 4A CARBA BETA LEVO GLYCEROPENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; DIISOPROPYL 1 (2 AMINO 6 AZIDOPURIN 9 YL) 5 O DIMETHOXYTRITYL 1,2,3 TRIDEOXY 3 AZA 4A CARBA BETA LEVO GLYCEROPENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; DIISOPROPYL 1 (2 AMINO 6 CHLOROPURIN 9 YL) 5 O DIMETHOXYTRITYL 1,2,3 TRIDEOXY 3 AZA 4A CARBA BETA LEVO GLYCEROPENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; DIISOPROPYL 1 (2,6 DIAMINOPURIN 9 YL) 5 O DIMETHOXYTRITYL 1,2,3 TRIDEOXY 3 AZA 4A CARBA BETA LEVO GLYCEROPENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; DIISOPROPYL 1 (ADENIN 9 YL) 5 O DIMETHOXYTRITYL 1,2,3 TRIDEOXY 3 AZA 4A CARBA BETA LEVO GLYCERO PENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; DIISOPROPYL 1 (CYTOSIN 1 YL) 5 O DIMETHOXYTRITYL 1,2,3 TRIDEOXY 3 AZA 4A CARBA BETA LEVO GLYCERO PENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; DIISOPROPYL 1 (CYTOSIN 2 O YL) 5 O DIMETHOXYTRITYL 1,2,3 TRIDEOXY 3 AZA 4A CARBA BETA LEVO GLYCEROPENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; DIISOPROPYL 1 (THYMIN 1 YL) 5 O DIMETHOXYTRITYL 1,2,3 TRIDEOXY 3 AZA 4A CARBA BETA LEVO GLYCERO PENTOFURANOS 3 YLMETHYLPHOSPHONIC ACID; NITROGEN; NUCLEOSIDE ANALOG; PROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ANIMAL CELL; ANTIVIRAL ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CONFORMATIONAL TRANSITION; CYTOTOXICITY; DIASTEREOISOMER; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PH MEASUREMENT; PRIORITY JOURNAL; PROTON TRANSPORT; SYNTHESIS;

EID: 57649095211     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.11.035     Document Type: Article

References (35)

1. Keith K.A., Hitchcock M.J.M., Lee W.A., Holy A., and Kern E.R. Antimicrob. Agents Chemother. 47 (2003) 2193-2198
2. De Clercq E., and Holy A. Nat. Rev. Drug Discovery 4 (2005) 928-940
3. Reiser, H.; Adrian S. R; Daniel B. T; William J. W; Gerald R. R. American Association for Cancer Research Annual Meeting: Proceedings, 2007.
4. Compton M.L., Toole J.J., and Paborsky L.R. Biochem. Pharmacol. 58 (1999) 709-714
5. Hickman D.T., King P.M., Cooper M.A., Slater J.M., and Micklefield J. Chem. Commun. (2000) 2251-2252
6. Hickman D.T., Tan T.H.S., Morral J., King P.M., Cooper M.A., and Micklefield J. Org. Biomol. Chem. 1 (2003) 3277-3292
7. Tan T.H.S., Worthington R.J., Pritchard R.G., Morral J., and Micklefield J. Org. Biomol. Chem. 5 (2007) 239-248
8. Worthington R.J., Bell N.M., Wong R., and Micklefield J. Org. Biomol. Chem. 6 (2008) 92-103
9. Harnden M.R., Jarvest R.L., and Parratt M.J. J. Chem. Soc., Perkin Trans. 1 (1992) 2259-2263
10. Adams D.R., Boyd A.S.F., Ferguson R., Grierson D.S., and Monneret C. Nucleosides Nucleotides Nucleic Acids 17 (1998) 1053-1075
11. 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
12. Chiacchio U., Iannazzo D., Piperno A., Romeo R., Romeo G., Rescifina A., and Saglimbeni M. Bioorg. Med. Chem. 14 (2006) 955-959
13. Chiacchio U., Rescifina A., Iannazzo D., Piperno A., Romeo R., Borrello L., Sciortino M.T., Balestrieri E., Macchi B., Mastino A., and Romeo G. J. Med. Chem. 50 (2007) 3747-3750
14. Sheikha G.A., La Colla P., and Loi A.G. Nucleos. Nucleot. Nucl. 21 (2002) 619-635
15. Declercq E. Rev. Med. Virol. 5 (1995) 149-164
16. Chakhmakhcheva O., Andrianov M., Buryakova A., Choob M., and Efimov V. Nucleosides Nucleotides 18 (1999) 1427-1428
17. Efimov V.A., Buryakova A.A., Choob M.V., and Chakhmakhcheva O.G. Nucleosides Nucleotides 18 (1999) 1393-1396
18. Efimov V.A., and Chakhmakhcheva O.G. (Special Issue). Collect. Czech. Chem. Commun. 5 (2002) 136-144
19. Ceulemans G., VanAerschot A., Wroblowski B., Rozenski J., Hendrix C., and Herdewijn P. Chem.-Eur. J. 3 (1997) 1997-2010
20. Robinson D.S., and Greenstein J.P. J. Biol. Chem. 195 (1952) 383-388
21. Baker G.L., Fritschel S.J., Stille J.R., and Stille J.K. J. Org. Chem. 46 (1981) 2954-2960
22. Verheijen J.C., van Roon A.M.M., van der Laan A.C., van der Marel G.A., and van Boom J.H. Nucleosides Nucleotides 18 (1999) 493-508
23. la Croce P., and La Rosa C. Tetrahedron: Asymmetry 13 (2002) 197-201
24. Gregson S.J., Howard P.W., Gullick D.R., Hamaguchi A., Corcoran K.E., Brooks N.A., Hartley J.A., Jenkins T.C., Patel S., Guille M.J., and Thurston D.E. J. Med. Chem. 47 (2004) 1161-1174
25. Gregson S.J., Howard P.W., Corcoran K.E., Barcella S., Yasin M.M., Hurst A.A., Jenkins T.C., Kelland L.R., and Thurston D.E. Bioorg. Med. Chem. Lett. 10 (2000) 1845-1847
26. Fields E.K. J. Am. Chem. Soc. 74 (1952) 1528-1531
27. Kocalka P., Pohl R., Rejman D., and Rosenberg I. Tetrahedron 62 (2006) 5763-5774
28. Altona C., and Sundaralingam M. J. Am. Chem. Soc. 94 (1972) 8205-8212
29. Haasnoot C.A.G., De Leeuw F.A.A.M., and Altona C. Tetrahedron 36 (1980) 2783-2792
30. Haasnoot C.A.G., De Leeuw F.A.A.M., De Leeuw H.P.M., and Altona C. Biopolymers 20 (1981) 1211-1245
31. Fache F., and Piva O. Tetrahedron: Asymmetry 14 (2003) 139-143
32. Levins C.G., and Schafmeister C.E. J. Am. Chem. Soc. 125 (2003) 4702-4703
33. Levins C.G., and Schafmeister C.E. J. Org. Chem. 70 (2005) 9002-9008
34. Andrus M.B., Li W.K., and Keyes R.F. J. Org. Chem. 62 (1997) 5542-5549
35. Lin C.C., Shimazaki M., Heck M.P., Aoki S., Wang R., Kimura T., Ritzen H., Takayama S., Wu S.H., WeitzSchmidt G., and Wong C.H. J. Am. Chem. Soc. 118 (1996) 6826-6840