Dideoxy fluoro-ketopyranosyl nucleosides as potent antiviral agents: Synthesis and biological evaluation of 2,3- and 3,4-dideoxy-3-fluoro-4- and -2-keto-β-d-glucopyranosyl derivatives of N4-benzoyl cytosine

European Journal of Medicinal Chemistry

Volumn 44, Issue 6, 2009, Pages 2696-2704

  Manta, Stella ^a   Tsoukala, Evangelia ^a   Tzioumaki, Niki ^a   Goropevšek, Aleš ^b   Pamulapati, Ravi Teja ^b   Cencič, Avrelija ^b   Balzarini, Jan ^c   Komiotis, Dimitri ^a  

^a UNIVERSITY OF THESSALY   (Greece)

^b UNIVERSITY OF MARIBOR   (Slovenia)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Antitumor activity; Antiviral; BrdU cell cycle; Dideoxy fluoro ketonucleosides; Flow cytometry; Gem diol

Indexed keywords

1 (2,3 DIDEOXY 3 FLUORO 6 O TRITYLBETA DEXTRO GLYCERO HEXOPYRANOSYL 4 ULOSE) N4 BENZOYL CYTOSINE; 1 (2,3 DIDEOXY 3 FLUORO BETA DEXTRO GLYCERO HEXOPYRANOSYL 4 ULOSE) N4 BENZOYL CYTOSINE; 1 (2,3 DIDEOXY 3 FLUORO BETA DEXTRO GLYCEROHEXOPYRANOSYL 4 ULOSE) N4 BENZOYL CYTOSINE; 1 (3,4 DIDEOXY 3 FLUORO 6 O TRITYL BETA DEXTRO GLYCERO HEXOPYRANOSYL 2 ULOSE) N4 BENZOYL CYTOSINE; 1 (3,4 DIDEOXY 3 FLUORO BETA DEXTRO GLYCEROHEXOPYRANOSYL 2 ULOSE) N4 BENZOYL CYTOSINE; 3 DEOXY 3 FLUORO DEXTRO GLUCOPYRANOSE; ANTIVIRUS AGENT; BROXURIDINE; FLUOROURACIL; N4 BENZOYL CYTOSINE; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ANIMAL CELL; ANTIVIRAL ACTIVITY; APOPTOSIS; ARTICLE; CELL CYCLE G1 PHASE; CELL CYCLE S PHASE; CONTROLLED STUDY; CYTOSTASIS; DNA VIRUS; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HYDRATION; NONHUMAN; POLYMERIZATION; RNA VIRUS; ROTAVIRUS; SILYLATION; VIRUS INFECTION;

ANTIVIRAL AGENTS; CYTOSINE; DOSE-RESPONSE RELATIONSHIP, DRUG; ENTEROVIRUS B, HUMAN; HELA CELLS; HERPESVIRUS 1, HUMAN; HERPESVIRUS 2, HUMAN; HUMANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR CONFORMATION; NUCLEOSIDES; RESPIRATORY SYNCYTIAL VIRUSES; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED; VACCINIA VIRUS; VESICULOVIRUS;

EID: 64549129103     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.01.020     Document Type: Article

References (63)

1. Voet D., and Voet J.G. Biochemistry. second ed. (1995), John Wiley & Sons, New York
2. Gumina G., Chong Y., Choo H., Song G., and Chu C.K. Curr. Top. Med. Chem. 2 (2002) 1065-1086
3. Orr D.C., Figueiredo H.T., Mo C.L., Penn C.R., and Cameron J.M. J. Biol. Chem. 267 (1992) 4177-4182
4. Kitade Y., Kozaki C., Miwa T., and Nakanishi M. Tetrahedron 58 (2002) 1271-1277
5. Turner M.A., Yang X., Yin D., Kuczera K., Borchardt R.T., and Howell P.L. Cell Biochem. Biophys. 33 (2000) 101-125
6. Anderson K.S. Biochim. Biophys. Acta 1587 (2002) 296-299
7. 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) 2607-2615
8. Baker C.H., Banzon J., Bollinger J.M., Stubbe J., Samano V., and Robins M.J. J. Med. Chem. 34 (1991) 1879-1884
9. Cory A.H., Samano V., Robins M.J., and Cory J.G. Biochem. Pharmacol. 47 (1994) 365-371
10. Plunkett W., Huang P., Xu Y.Z., Heinemann V., Gunewald R., and Gandhi V. Semin. Oncol. 22 Suppl. 11 (1995) 3-10 and references cited therein
11. 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) 4183-4189
12. Azuma A., Hanaoka K., Kurihara A., Kobayashi T., Miyaushi S., Kamo N., Tanaka M., Sasaki T., and Matsuda A. J. Med. Chem. 38 (1995) 3391-3397
13. Matsuda A., and Azuma A. Nucleosides Nucleotides 14 (1995) 461-471
14. Verheggen I., Van Aerschot A., Toppet S., Snoeck R., Janssen G., Balzarini J., De Clercq E., and Herdewijn P. J. Med. Chem. 36 (1993) 2033-2040
15. 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) 826-835
16. 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) 4343-4353
17. Agelis G., Tzioumaki N., Tselios T., Botić T., Cencič A., and Komiotis D. Eur. J. Med. Chem. 43 (2008) 1366-1375
18. Agelis G., Tzioumaki N., Botić T., Cencič A., and Komiotis D. Bioorg. Med. Chem. 15 (2007) 5448-5456
19. Haouz A., Vanheusden V., Munier-Lechman H., Froeyen M., Herdewijn P., Van Galenbergh S., and Delarue M. J. Biol. Chem. 278 (2003) 4963-4971
20. Spanou C., Manta S., Komiotis D., Dervishi A., and Kouretas D. Int. J. Mol. Sci. 8 (2007) 695-704
21. Vastmans K., Pochet S., Peys A., Kerremans L., Van Aerschot A., Hendrix C., Marliere P., and Herdewijn P. Biochemistry 39 (2000) 12757-12765
22. Vastmans K., Froeyen M., Kerremans L., Pochet S., and Herdewijn P. Nucleic Acids Res. 29 (2001) 3154-3163
23. Egron M.J., Leclercq F., Antonakis K., Bennani-Baiti I., and Frayssinet C. Carbohydr. Res. 248 (1993) 143-150
24. Paterson J., Uriel C., Egron M.J., Herscovici J., Antonakis K., and Alaoui M. Antimicrob. Agents Chemother. 42 (1998) 779-784
25. Alaoui M., Lasne C., Antonakis K., and Chouroulinkov I. Mutagenesis 6 (1986) 411-417
26. Khan A.R., Mulligan K.X., Redda K.K., and Ollapally A.P. Synth. Commun. 32 (2002) 1023-1030
27. Alaoui M., Egron M.J., Bessodes M., Antonakis K., and Chouroulinkov I. Eur. J. Med. Chem. 22 (1987) 305-310
28. Aujard C., Moule Y., Chany-Morel E., and Antonakis K. Biochem. Pharmacol. 27 (1978) 1037-1042
29. Halmos T., Cardon A., and Antonakis K. Chem. Biol. Interact. 46 (1983) 11-29
30. Antonakis K., and Chouroulinkov I. C.R. Acad. Sci. Paris 273D (1971) 2661-2663
31. Antonakis K., and Chouroulinkov I. Biochem. Pharmacol. 23 (1974) 2095-2100
32. Antonakis K., Halmos T., Bach J., and Chouroulinkov I. Eur. J. Med. Chem. 15 (1980) 237-240
33. Chouroulinkov I., and Antonakis K. C.R. Acad. Sci. Hebd Seances Acad. Sci. D 285 (1977) 1021-1024
34. Liu P., Sharon A., and Chu C.K. J. Fluorine Chem. 129 (2008) 743-766
35. Lee K., Choi Y., Gumina G., Zhou W., Schinazi R.F., and Chu C.K. J. Med. Chem. 45 (2002) 1313-1320
36. Chong Y., Choo H., Lee S., Choi Y., Schinazi R.F., and Chu C.K. J. Med. Chem. 45 (2002) 4888-4898
37. Pankiewicz K.W. Carbohydr. Res. 327 (2000) 87-105
38. 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) 1712-1715
39. Tsoukala E., Agelis G., Dolinsek J., Botić T., Cencič A., and Komiotis D. Bioorg. Med. Chem. 15 (2007) 3241-3247
40. Manta S., Agelis G., Botić T., Cencič A., and Komiotis D. Bioorg. Med. Chem. 15 (2007) 980-987
41. Manta S., Agelis G., Botić T., Cencič A., and Komiotis D. Eur. J. Med. Chem. 43 (2008) 420-428
42. Pérez-Pérez M.J., De Clercq E., and Herdewijn P. Bioorg. Med. Chem. Lett. 6 (1996) 1457-1460
43. Augustyns K., Vandendriessche F., Van Aerschot A., Busson R., Urbanke C., and Herdewijn P. Nucleic Acids Res. 20 (1992) 4711-4716
44. Augustyns K., Rozenski J., Van Aerschot A., Busson R., Claes P., and Herdewijn P. Tetrahedron 50 (1994) 1189-1198 and references cited therein
45. Augustyns K., Rozenski J., Van Aerschot A., Janssen G., and Herdewijn P. J. Org. Chem. 58 (1993) 2977-2982
46. Sowa W., and Thomas H.S. Can. J. Chem. 44 (1966) 836-837
47. Foster A.B., Hems R., and Webber M.J. Carbohydr. Res. 5 (1967) 292-301
48. Dunkel M., and Pfleiderer W. Nucleosides Nucleotides 11 (1992) 787-819
49. Robins M.J., Wilson J.S., and Hansske F. J. Am. Chem. Soc. 105 (1983) 4059-4065
50. Chien T.-C., Chen C.-S., and Chern J.-W. J. Chin. Chem. Soc. 52 (2005) 1237-1244
51. Barton D.H.R., and McCombie S.W. J. Chem. Soc., Perkin Trans. 1 16 (1975) 1574-1585
52. Leclercq F., Egron M.J., Antonakis K., Bennani-Baiti I., and Frayssinet C. Carbohydr. Res. 228 (1992) 95-102
53. Milecki J., Foldesi A., Fischer A., Adamiak R.W., and Chattopadhyaya J. J. Labelled Cpd Radiopharm. 44 (2001) 763-783
54. Gutzwiller J., and Uskokovic M. J. Am. Chem. Soc. 92 (1970) 204-205
55. Boger D.L., and Machiya K. J. Am. Chem. Soc. 114 (1992) 10056-10058
56. Matsuda A., and Sasaki T. Cancer Sci. 95 (2004) 105-111
57. Peters G.J., Van der Wilt C.L., Van Triest B., Codacci-Pisanelli G., Johnston P.G., Van Groeningen C.J., and Pinedo H.M. Eur. J. Cancer 31A (1995) 1299-1305
58. Pinedo H.M., and Peters G.F. J. Clin. Oncol. 6 (1988) 1653-1664
59. Pickard M., Dive C., and Kinsella A.R. Br. J. Cancer 72 (1995) 1389-1396
60. Piazza G.A., Rahm A.K., Finn T.S., Fryer B.H., Li H., Stoumen A.L., Pamukcu R., and Ahnen D.J. Cancer Res. 57 (1997) 2452-2459
61. Komiotis D., Agelis G., Manta S., Tzioumaki N., and Tsoukala E. J. Carbohydr. Chem. 25 (2006) 441-450
62. Tsurusawa M., Niwa M., Katano N., and Fujimoto T. Cancer Res. 48 (1988) 4288-4293
63. Tonkinson J.L., Marder P., Andis S.L., Schultz R.M., Gossett L.S., Shih C., and Mendelsohn L.G. Cancer Chemother. Pharmacol. 39 (1997) 521-531