Small libraries of fused quinazolinone-sugars. Access to quinazolinedione nucleosides

Tetrahedron

Volumn 60, Issue 11, 2004, Pages 2609-2619

  Girniene, Jolanta ^a,b   Apremont, Guillaume ^a   Tatibouët, Arnaud ^a   Sackus, Algirdas ^b   Rollin, Patrick ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b KAUNAS UNIVERSITY OF TECHNOLOGY   (Lithuania)

Author keywords

1,3 Oxazolidine 2 thione; Anthranilic acid; Nucleoside; Quinazolinedione; Quinazolinone

Indexed keywords

3 (2' DEOXY BETA DEXTRO RIBOFURANOSYL) 2,4 QUINAZOLINEDIONE; 3 (3',5' DI O BENZYL 2' DEOXY BETA DEXTRO RIBOFURANOSYL) 2,4 QUINAZOLINEDIONE; 3 (3',5' DI O BENZYL BETA DEXTRO ARABINOSYL) 2,4 QUINAZOLINEDIONE; 3 (3',5' DI O BENZYL BETA DEXTRO RIBOSYL) 2,4 QUINAZOLINEDIONE; 3 BETA DEXTRO ARABINOSYL 2,4 QUINAZOLINEDIONE; 3 BETA DEXTRO RIBOSYL 2,4 QUINAZOLINEDIONE; ANTHRANILIC ACID DERIVATIVE; CARBOHYDRATE DERIVATIVE; NUCLEOSIDE DERIVATIVE; O 2,O 2' ANHYDRO 3 (3',5' DI O BENZYL ALPHA DEXTRO XYLOFURANOSYL) 2,4 QUINAZOLINEDIONE; O 2,O 2' ANHYDRO 3 (3',5' DI O BENZYL ALPHA LEVO ARABINOFURANOSYL) 2,4 QUINAZOLINEDIONE; O 2,O 2' ANHYDRO 3 (3',5' DI O BENZYL BETA DEXTRO ARABINOFURANOSYL) 2,4 QUINAZOLINEDIONE; O 2,O 2' ANHYDRO 3 (3',5' DI O BENZYL BETA DEXTRO ARABINOFURANOSYL) 6 BROMO 2,4 QUINAZOLINEDIONE; O 2,O 2' ANHYDRO 3 (3',5' DI O BENZYL BETA DEXTRO ARABINOFURANOSYL) 6 IODO 2,4 QUINAZOLINEDIONE; O 2,O 2' ANHYDRO 3 (3',5' DI O BENZYL BETA DEXTRO ARABINOFURANOSYL) 6 METHYL 2,4 QUINAZOLINEDIONE; O 2,O 2' ANHYDRO 3 (3',5' DI O BENZYL BETA DEXTRO RIBOFURANOSYL) 2,4 QUINAZOLINEDIONE; O 2,O 2' ANHYDRO 3 (3',5' DI O TERT BUTYLDIMETHYLSILYL BETA DEXTRO ARABINOFURANOSYL) 2,4 QUINAZOLINEDIONE; O 2,O 2' ANHYDRO 3 (3',5' DI O TERT BUTYLDIMETHYLSILYL BETA LEVO ARABINOFURANOSYL) 2,4 QUINAZOLINEDIONE; O 2,O 2' ANHYDRO 3 (3',5',6' TRI O TERT BUTYLDIMETHYLSILYL BETA DEXTRO GLUCOFURANOSYL) 2,4 QUINAZOLINEDIONE; O 2,O 3' ANHYDRO 3 (1',4',6' TRI O BENZYL BETA DEXTRO FRUCTOFURANOSYL) 2,4 QUINAZOLINEDIONE; OXAZOLINE DERIVATIVE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG SYNTHESIS; POLYMERIZATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 1342302798     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.01.032     Document Type: Article

References (39)

1. Agrofoglio L., Challand S.R. Acyclic, carbocyclic and L-nucleosides. 1998;Kluwer, London.
2. Rando R.F., Nguyen-Ba N. Drug Discov. Today. 5:2000;465-476.
3. McGuigan C., Yarnold C.J., Jones G., Velazquez S., Barucki H., Brancale A., Andrei G., Snoeck R., De Clercq E., Balzarini J. J. Med. Chem. 42:1999;4479-4484.
4. Brancale A., McGuigan C., Andrei G., Snoeck R., DeClercq E., Balzarini J. Bioorg. Med. Chem. Lett. 10:2000;1215-1217.
5. Harwood E.A., Hopkins P.B., Sigurdsson S. J. Org. Chem. 65:2000;2959-2964.
6. Kotera M., Roupioz Y., Defrancq E., Bourdat A.-G., Garcia J., Coulombeau C.J. Chem. Eur. J. 6:2000;4163-4169.
7. Suzuki T., Ohshimo H. FEBS Lett. 516:2002;67-70.
8. Trévisiol E., Defrancq E., Lhomme J., Laayoun A., Cros P. Eur. J. Org. Chem. 1:2000;211-217.
9. Kool E.T., Morales J.C., Guckian K.M. Angew. Chem. Int. Ed. 39:2000;990-1009.
10. Kool E.T. Curr. Opin. Chem. Biol. 4:2000;602-608.
11. Martinez Gimenez J.A., Saez G.T., Tabraes Seisdedos R. J. Theor. Biol. 194:1998;485-490.
12. Saito Y., Nakamura M., Ohno T., Chaicharoenpong C., Ichikawa E., Yamamura S., Kato K., Umezawa K. J. Chem. Soc. Perkin Trans. 1. 2001;298-304.
13. Kandimalla E.R., Yu D., Zhao Q., Agrawal S. Bioorg. Med. Chem. 9:2001;807-813.
14. Sauer D.R., Schneller S.W. Synthesis. 1991;747-750.
15. Al Mourabit A., Beckmann M., Poupat C., Ahond A., Potier P. Tetrahedron: Asymmetry. 7:1996;3455-3464.
16. Lengeler D., Weisz K. Tetrahedron Lett. 42:2001;1479-1481.
17. Jungmann O., Pfleiderer W. Tetrahedron Lett. 37:1996;8355-8358.
18. Rösler A., Pfleiderer W. Helv. Chim. Acta. 80:1997;1869-1881.
19. Wang Z., Rizzo C. J. Org. Lett. 2:2000;227-230.
20. El Ashry E.S.H., Awad L.F., Winkler M. J. Chem. Soc., Perkin Trans. 1. 2000;829-834.
21. Loakes D., Guo M.-J., Yang J.-C., Brown D.M. Helv. Chim. Acta. 83:2000;1693-1700.
22. Bertolini R., Hunziker J. Helv. Chim. Acta. 83:2000;1962-1976.
23. Wu W., Bergstrom D.E. J. Org. Chem. 68:2003;3860-3865.
24. Jungmann O., Pfleiderer W. Tetrahedron Lett. 37:1996;8355-8358.
25. Guckian K.M., Morales J.C., Kool E.T. J. Org. Chem. 63:1998;9652-9656.
26. Sugimura H., Osumi K., Kodaka Y., Sujino K. J. Org. Chem. 59:1994;7653-7660.
27. Gosselin G., Bergogne M.-C., De Rudder J., De Clercq E., Imbach J.-L. J. Med. Chem. 29:1986;203-213.
28. Mourier N.S., Eleuteri A., Hurwitz S.J., Tharnish P.M., Shinazi R.F. Bioorg. Med. Chem. 7:1999;2759-2766.
29. Stout M.G., Robins R.K. J. Org. Chem. 33:1968;1219-1225.
30. Dunkel M., Pfleiderer W. Nucleosides Nucleotides. 11:1992;787-919.
31. El-Barbary A.A., El-Brollosy R., Pedersen E.B. Bull. Soc. Chim. Fr. 133:1996;51-57.
32. Sauter F., Fröhlich J., Blasl K., Gewald K. Heterocycles. 40:1995;851.
33. Preshad M., Chen L., Repic O., Blacklock T.J. Synth. Commun. 28:1998;2125.
34. Alexandre F.R., Berecibar A., Wrigglesworth R., Besson T. Tetrahedron. 59:2003;1413-1419.
35. Leoni O., Bernardi R., Gueyrard D., Rollin P., Palmieri S. Tetrahedron: Asymmetry. 10:1999;4775.
36. Gueyrard D., Grumel V., Leoni O., Palmieri S., Rollin P. Heterocycles. 52:2000;827.
37. Gueyrard D., Leoni O., Palmieri S., Rollin P. Tetrahedron: Asymmetry. 12:2001;337-340.
38. Girniene J., Gueyrard D., Tatibouët A., Sackus A., Rollin P. Tetrahedron Lett. 42:2001;2977-2980.
39. Bromund W., Herbst R.M. J. Org. Chem. 1945;267-269.