Fluoro-ketopyranosyl nucleosides: Synthesis and biological evaluation of 3-fluoro-2-keto-β-d-glucopyranosyl derivatives of N4-benzoyl cytosine

Bioorganic and Medicinal Chemistry

Volumn 15, Issue 2, 2007, Pages 980-987

  Manta, Stella ^a   Agelis, George ^a   Botić, Tanja ^b   Cencič, Avrelija ^b   Komiotis, Dimitri ^a  

^a UNIVERSITY OF THESSALY   (Greece)

^b UNIVERSITY OF MARIBOR   (Slovenia)

Author keywords

elimination reaction; Antitumor activity; Antiviral; Gem diol; Unsaturated fluoro ketonucleosides

Indexed keywords

1 (3 DEOXY 3 FLUORO 2,4,6 TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL) N4 BENZOYLCYTOSINE; 1 (3 DEOXY 3 FLUORO 4,6 O ISOPROPYLIDENE BETA DEXTRO GLUCOPYRANOSYL 2 ULOSE) N4 BENZOYLCYTOSINE; 1 (3 DEOXY 3 FLUORO 4,6 O ISOPROPYLIDENE BETA DEXTRO GLUCOPYRANOSYL) N4 BENZOYLCYTOSINE; 1 (3,4 DIDEOXY 3 FLUORO BETA DEXTRO GLUCOPYRANOSYL) N4 BENZOYLCYTOSINE; 1 (3,4 DIDEOXY 3 FLUORO BETA DEXTRO GLYCEROHEX 3 ENOPYRANOSYL 2 ULOSE) N4 BENZOYLCYTOSINE; 1 (6 O ACETYL 3,4 DIDEOXY 3 FLUORO BETA DEXTRO GLYCEROHEX 3 ENOPYRANOSYL 2 ULOSE) N4 BENZOYLCYTOSINE; NUCLEOSIDE DERIVATIVE; ZIDOVUDINE;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; CELL STRAIN CACO 2; CONTROLLED STUDY; CYTOTOXICITY; DEACYLATION; DRUG SYNTHESIS; EVALUATION; FLUORINATION; HUMAN; HUMAN CELL; NONHUMAN; ROTAVIRUS; SILYLATION; VESICULAR STOMATITIS VIRUS;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CACO-2 CELLS; CATTLE; CELL LINE; CELL LINE, TUMOR; CELL PROLIFERATION; CYTOSINE; DRUG SCREENING ASSAYS, ANTITUMOR; HAPLORHINI; HUMANS; INDICATORS AND REAGENTS; MONOSACCHARIDES; OXIDATION-REDUCTION; SWINE; VESICULAR STOMATITIS-INDIANA VIRUS; ZIDOVUDINE;

ROTAVIRUS; VESICULAR STOMATITIS VIRUS;

EID: 33845286570     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.10.033     Document Type: Article

References (60)

1. Zhou W., Gumina G., Chong Y., Wang J., Shinazi R.F., and Chu C.K. J. Med. Chem. 47 (2004) 3399
2. Perigaud C., Gosselin G., and Imbach J.L. Nucleosides Nucleotides 11 (1992) 903
3. Robins R.K., and Kini G.D. Purines and purine nucleoside analogues as antitumor agents. In: Wilman D.E.V. (Ed). The Chemistry of Antitumor Agents (1990), Chapman and Hall, New York 299-321
4. MacCoss M., and Robins M.J. Anticancer pyrimidines, pyrimidine nucleosides and prodrugs. In: Wilman D.E.V. (Ed). The chemistry of Antitumor Agents (1990), Chapman and Hall, New York 261-298
5. Clark J.L., Mason J.C., Hollecker L., Stuyver L.J., Tharnish P.M., McBrayer T.R., Otto M.J., Furman A.P., Schinazi R.F., and Watanabe K.A. Bioorg. Med. Chem. Lett. 16 (2006) 1712
6. Kumar P., Ohkura K., Balzarini J., De Clerq E., Seki K., and Wiebe L.I. Nucleosides, Nucleotides & Nucleic Acids 23 (2004) 7
7. Fuentes J., Angulo M., and Pradera M.A. J. Org. Chem. 67 (2002) 2577
8. Van Aerschot A., Herdewijn P., Balzarini J., Pawels R., and De Clerq E. J. Med. Chem. 32 (1989) 1743
9. Blandin M., Son T.-D., Catlin J.C., and Guschlbauer W. Biochim. Biophys. Acta 361 (1974) 249
10. Morton G.O., Lancaster J.E., Van Lear G.E., Fulmor W., and Meyer W.E. J. Am. Chem. Soc. 91 (1969) 1535
11. Lipnick R.L., and Fissekis J.D. Biochim. Biophys. Acta 608 (1980) 96
12. Takenuki K., Matsuda A., Ueda T., Sasaki T., Fujii A., and Yamagami K. J. Med. Chem. 31 (1988) 1063
13. Matsuda A., Takenuki K., Sasaki T., and Ueda T. J. Med. Chem. 34 (1991) 812
14. Yamagami K., Fujii A., Arita M., Okumoto T., Sakata S., Matsuda A., Ueda T., and Sasaki T. Cancer Res. 51 (1991) 2319
15. Lin T.S., Luo M.Z., Liu M.C., Clarkatzenburg R.H., Cheng Y.C., Prusoff W.H., Mancini W.R., Birnbaum G.I., Gabe E., and Giziewicz J. J. Med. Chem. 34 (1991) 2607
16. Baker C.H., Banzon J., Bollinger J.M., Stubbe J., Samano V., and Robins M.J. J. Med. Chem. 34 (1991) 1879
17. Cory A.H., Samano V., Robins M.J., and Cory J.G. Biochem. Pharmacol. 47 (1994) 365
18. Plunkett, W.; Huang, P.; Xu, Y. Z.; Heinemann, V.; Grunewald, R.; Gandhi, V. Semin. Oncol. 1995, 22, 3-10 (Suppl. 11) and references cited therein.
19. Matsuda A., Nakajima Y., Azuma A., Tanaka M., and Sasaki T. J. Med. Chem. 34 (1991) 2917
20. Azuma A., Nakajima Y., Nishizono N., Minakawa N., Suzuki M., Hanaoka K., Kobayashi T., Tanaka M., Sasaki T., and Matsuda A. J. Med. Chem. 36 (1993) 4183
21. Tanaka M., Matsuda A., Terao T., and Sasaki T. Cancer Lett. 64 (1992) 67
22. Azuma A., Hanaoka K., Kurihara A., Kobayashi T., Miyaushi S., Kamo N., Tanaka M., Sasaki T., and Matsuda A. J. Med. Chem. 38 (1995) 3391
23. Matsuda A., and Azuma A. Nucleosides Nucleotides 14 (1995) 461
24. Schinazi R.F., Mellors J., Bazmi H., Diamond S., Garber S., Gallagher K., Geleziunas R., Klabe R., Pierce M., Rayner M., Wu J.T., Zhang H., Hammond J., Bacheler L., Manion D.J., Otto M.J., Stuyver L., Trainor G., Liotta D.C., and Erickson-Viitanen S. Antimicrob. Agents Chemother. 46 (2002) 1394
25. Lin T.S., Luo M.Z., Liu M.C., Zhu Y.L., Gullen E., Dutschman G.E., and Cheng Y.C. J. Med. Chem. 39 (1996) 1757
26. Chong Y., Gumina G., Mathew J.S., Schinazi R.F., and Chu C.K. J. Med. Chem. 46 (2003) 3245
27. Verheggen I., Van Aerschot A., Toppet S., Snoeck R., Janssen G., Balzarini J., De Clercq E., and Herdewijn P. J. Med. Chem. 36 (1993) 2033
28. Verheggen I., Van Aerschot A., Van Meervelt L., Rozenski J., Wiebe L., Snoeck R., Andrei G., Balzarini J., Claes P., De Clercq E., and Herdewijn P. J. Med. Chem. 38 (1995) 826
29. Ostrowski T., Wroblowski B., Busson R., Rozenski J., De Clercq E., Bennet M.S., Champness J.N., Summers W.C., Sanderson M.R., and Herdewijn P. J. Med. Chem. 41 (1998) 4343
30. Maurinsh Y., Schraml J., De Winter H., Blaton N., Peeters O., Lescrinier E., Rozenski J., Van Aerschot A., De Clercq E., Busson R., and Herdewijn P. J. Org. Chem. 62 (1997) 2861
31. Haouz A., Vanheusden V., Munier-Lechman H., Froeyen M., Herdewijn P., Van Galenbergh S., and Delarue M. J. Biol. Chem. 278 (2003) 4963
32. Vastmans K., Pochet S., Peys A., Kerremans L., Van Aerschot A., Hendrix C., Marliere P., and Herdewijn P. Biochemistry 39 (2000) 12757
33. Vastmans K., Froeyen M., Kerremans L., Pochet S., and Herdewijn P. Nucleic Acids Res. 29 (2001) 3154
34. Paterson J., Uriel C., Egron M.J., Herscovici J., Antonakis K., and Alaoui M. Antimicrob. Agents Chemother. 42 (1998) 779
35. Alaoui M., Lasnes C., Antonakis K., and Chouroulinkov I. Mutagenesis 1 (1986) 411
36. Alaoui M., Egron M.J., Bessodes M., Antonakis K., and Chouroulinkov I. Eur. J. Med. Chem. 22 (1987) 305
37. Antonakis K., and Chouroulinkov I. Biochem. Pharmacol. 23 (1974) 2095
38. Halmos T., Cardon A., and Antonakis K. Chem. Biol. Interact. 46 (1983) 11
39. Antonakis K., Halmos T., Bach J., and Chouroulinkov I. Eur. J. Med. Chem. 15 (1980) 237
40. Chouroulinkov I., and Antonakis K. C.R. Acad. Sci. Hebd Seances Acad, Sci, D 285 (1977) 1021
41. Antonakis K. Chimia 29 (1975) 59
42. Antonakis K., and Egron M.J. Carbohydr. Res. 27 (1973) 468
43. Leclercq F., Egron M.J., Antonakis K., Bennani-Baiti I., and Frayssinet C. Carbohydr. Res. 228 (1992) 95
44. Sowa W., and Thomas H.S. Can. J. Chem. 44 (1966) 836
45. Foster A.B., Hems R., and Webber M.J. Carbohyd. Res. 5 (1967) 292
46. Milecki J., Foldesi A., Fischer A., Adamiak R.W., and Chattopadhyaya J. J. Labelled Compd. Radiopharm. 44 (2001) 763
47. Neilson T., and Werstiuk E.S. Can. J. Chem. 49 (1971) 493
48. Plattner J.J., Gless R.D., and Rapoport H. J. Am. Chem. Soc. 94 (1972) 8613
49. Kunesch N., Meit C., and Poisson J. Tetrahedron Lett. 28 (1987) 3569
50. Herscovici J., and Antonakis K. J. Chem. Soc. Chem. Commun. 12 (1979) 561
51. Natraza A., Ferrara J.D., Youngs W.J., and Sukenik C.N. J. Am. Chem. Soc. 109 (1987) 7477
52. Mancuso A.J., Huang S.L., and Swern D. J. Org. Chem. 43 (1978) 2480
53. Egron M.J., Leclercq F., Antonakis K., Bennani-Baiti I., and Frayssinet C. Carbohydr. Res. 248 (1993) 143
54. Egron M.J., Dorange I., Antonakis K., Herscovici J., and Ollapally A.P. Nucleosides, Nucleotides & Nucleic Acids 21 (2002) 327
55. Egron M.J., Komiotis D., Dorange I., Herscovici J., Ollapally A.P., and Antonakis K. Nucleosides, Nucleotides & Nucleic Acids 24 (2005) 243
56. Byramova N.E., Ovchinnikov M.V., Backinowsky L.V., and Kochetkov N.K. Carbohydr. Res. 124 (1983) c8-c11
57. Allard P., Dinh T.H., Gouyette C., Igolen J., Chermann J.C., and Barre-Sinoussi F. J. Med. Chem. 24 (1981) 1291
58. Robins M.J., Samano V., Zhang W., Balzarini J., De Clercq E., Borechardt R.T., Lee Y., and Yuan C.S. J. Med. Chem. 35 (1992) 2283
59. Kitaoka S., Suzuki H., Numazaki Y., Konno T., and Ishida N. Tohoku. J. Exp. Med. 149 (1986) 437
60. Cencič A., Henry C., Lefèvre F., Huet J.H., Koren S., and La Bonnardière C. Eur. J. Biochem. 269 (2002) 2772