Synthesis and biological evaluation of unsaturated keto and exomethylene d-arabinopyranonucleoside analogs: Novel 5-fluorouracil analogs that target thymidylate synthase

European Journal of Medicinal Chemistry

Volumn 46, Issue 4, 2011, Pages 993-1005

  Tzioumaki, Niki ^a   Manta, Stella ^a   Tsoukala, Evangelia ^a   Voorde, Johan Vande ^b   Liekens, Sandra ^b   Komiotis, Dimitri ^a   Balzarini, Jan ^b  

^a UNIVERSITY OF THESSALY   (Greece)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

5 Fluorouracil prodrugs; Antiviral; Chemotherapy; Cytotoxicity; Ketonucleosides; Unsaturated nucleosides

Indexed keywords

1 (2 DEOXY 2 METHYLENE ALPHA DEXTRO ERYTHROPENTOPYRANOSYL) 5 FLUOROURACIL; 1 (2 DEOXY 2 METHYLENE ALPHA DEXTRO ERYTHROPENTOPYRANOSYL)THYMINE; 1 (2 DEOXY 2 METHYLENE ALPHA DEXTRO ERYTHROPENTOPYRANOSYL)URACIL; 1 (2,3,4 TRIDEOXY 2 METHYLENE ALPHA PENT 2 ENOPYRANOSYL) 5 FLUOROURACIL; 1 (2,3,4 TRIDEOXY 2 METHYLENE ALPHA PENT 2 ENOPYRANOSYL) N4 BENZOYLCYTOSINE; 1 (2,3,4 TRIDEOXY 2 METHYLENE ALPHA PENT 2 ENOPYRANOSYL)CYTOSINE; 1 (2,3,4 TRIDEOXY 2 METHYLENE ALPHA PENT 2 ENOPYRANOSYL)THYMINE; 1 (2,3,4 TRIDEOXY 2 METHYLENE ALPHA PENT 2 ENOPYRANOSYL)URACIL; 1 (3,4 DIDEOXY ALPHA PENT 3 ENOPYRANOSYL 2 ULOSE) 5 (TRIFLUOROMETHYL)URACIL; 1 (3,4 DIDEOXY ALPHA PENT 3 ENOPYRANOSYL 2 ULOSE) 5 FLUOROURACIL; 1 (3,4 DIDEOXY ALPHA PENT 3 ENOPYRANOSYL 2 ULOSE) N4 BENZOYLCYTOSINE; 1 (3,4 DIDEOXY ALPHA PENT 3 ENOPYRANOSYL 2 ULOSE)THYMINE; 1 (3,4 DIDEOXY ALPHA PENT 3 ENOPYRANOSYL 2 ULOSE)URACIL; FLUOROURACIL DERIVATIVE; PYRIMIDINE NUCLEOSIDE DERIVATIVE; THYMIDYLATE SYNTHASE; UNCLASSIFIED DRUG;

ACETYLATION; ANIMAL CELL; ARTICLE; CARCINOMA CELL; CONTROLLED STUDY; COXSACKIE VIRUS B4; CYTOSTASIS; DEACETYLATION; DRUG SYNTHESIS; GROWTH INHIBITION; HELA CELL; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; IC 50; LEUKEMIA L 1210; MAMMALIAN ORTHOREOVIRUS; NONHUMAN; PARAINFLUENZA VIRUS 3; RESPIRATORY SYNCYTIAL PNEUMOVIRUS; SILYLATION; SINDBIS VIRUS; VACCINIA VIRUS; VESICULAR STOMATITIS VIRUS; VIRUS INHIBITION;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CELL LINE, TUMOR; ENZYME INHIBITORS; FLUOROURACIL; HUMANS; INHIBITORY CONCENTRATION 50; MICE; NUCLEOSIDES; SUBSTRATE SPECIFICITY; THYMIDYLATE SYNTHASE; URIDINE PHOSPHORYLASE; VIRUSES;

EID: 79952281166     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.01.005     Document Type: Article

References (52)

1. A. Holý Antiviral Res. 71 2006 248 253
2. R.C. Brandy, and D.I. Bernstein Antiviral Res. 61 2004 73 81
3. D.C. Meadows, and J. Gervay-Hague Chem. Med. Chem. 1 2006 16 29
4. C. Mathé, and G. Gosselin Antiviral Res. 71 2006 276 281
5. R.F. Schinazi, B.I. Hernandez-Santiago, and S.J. Hurwitz Antiviral Res. 71 2006 322 334
6. D. Komiotis, S. Manta, E. Tsoukala, and N. Tzioumaki Curr. Med. Chem. Anti-Infect. Agents 7 2008 219 244
7. W.D. Meng, and F.L. Qing Curr. Top. Med. Chem. 6 2006 1499 1528
8. G.V. Papatheodoridis, E. Dimou, and V. Papadimitropoulos Am. J. Gastroenterol. 97 2002 1618 1628
9. I. Verheggen, A. Van Aerschot, L. Van Meervelt, J. Rozenski, L. Wiebe, R. Snoeck, G. Andrei, J. Balzarini, P. Claes, E. De Clercq, and P. Herdewijn J. Med. Chem. 38 1995 826 835
10. T. Ostrowski, B. Wroblowski, R. Busson, J. Rozenski, E. De Clercq, M.S. Bennet, J.N. Champness, W.C. Summers, M.R. Sanderson, and P. Herdewijn J. Med. Chem. 41 1998 4343 4353
11. Y. Maurinsh, J. Schraml, H. De Winter, N. Blaton, O. Peeters, E. Lescrinier, J. Rozenski, A. Van Aerschot, E. De Clercq, R. Busson, and P. Herdewijn J. Org. Chem. 62 1997 2861 2871
12. C. Spanou, S. Manta, D. Komiotis, A. Dervishi, and D. Kouretas Int. J. Mol. Sci. 8 2007 695 704
13. A. Haouz, V. Vanheusden, H. Munier-Lechman, M. Froeyen, P. Herdewijn, S. Van Galenbergh, and M. Delarue J. Biol. Chem. 278 2003 4963 4971
14. K. Vastmans, S. Pochet, A. Peys, L. Kerremans, A. Van Aerschot, C. Hendrix, P. Marliere, and P. Herdewijn Biochemistry 39 2000 12757 12765
15. K. Vastmans, M. Froeyen, L. Kerremans, S. Pochet, and P. Herdewijn Nucleic Acids Res. 29 2001 3154 3163
16. P. Herdewijn, and E. De Clercq Bioorg. Med. Chem. Lett. 11 2001 1591 1597
17. M.J. Egron, F. Leclercq, K. Antonakis, I. Bennani-Baiti, and C. Frayssinet Carbohydr. Res. 248 1993 143 150
18. M. Alaoui, M.J. Egron, M. Bessodes, K. Antonakis, and I. Chouroulinkov Eur. J. Med. Chem. 22 1987 305 310
19. F. Leclercq, and K. Antonakis Carbohydr. Res. 263 1994 309 313
20. G.S. Bisacchi, S.T. Chao, C. Bachard, J.P. Daris, S. Innaimo, G.A. Jacobs, O. Kocy, P. Lapointe, A. Martel, Z. Merchant, W.A. Slusarchyk, J.E. Sundeen, M.G. Young, R. Colonno, and R. Zahler Bioorg. Med. Chem. Lett. 7 1997 127 132
21. S.J. Yoo, H.O. Kim, Y. Lim, J. Kim, and L.S. Jeong Bioorg. Med. Chem. 10 2002 215 226
22. P. Gunaga, M. Baba, and L.S. Jeong J. Org. Chem. 69 2004 3208 3211
23. F. Leclercq, and K. Antonakis Carbohydr. Res. 181 1988 217 222
24. S. Manta, G. Agelis, T. Botić, A. Cencič, and D. Komiotis Bioorg. Med. Chem. 15 2007 980 987
25. S. Manta, G. Agelis, T. Botić, A. Cencič, and D. Komiotis Eur. J. Med. Chem. 43 2008 420 428
26. S. Manta, E. Tsoukala, N. Tzioumaki, A. Goropevšek, R.T. Pamulapati, A. Cencič, J. Balzarini, and D. Komiotis Eur. J. Med. Chem. 44 2009 2696 2704
27. S. Manta, E. Tsoukala, N. Tzioumaki, C. Kiritsis, J. Balzarini, and D. Komiotis Bioorg. Chem. 38 2010 48 55
28. S. Manta, N. Tzioumaki, E. Tsoukala, A. Panagiotopoulou, M. Pelecanou, J. Balzarini, and D. Komiotis Eur. J. Med. Chem. 44 2009 4764 4771
29. G. Agelis, N. Tzioumaki, T. Botić, A. Cencič, and D. Komiotis Bioorg. Med. Chem. 15 2007 5448 5456
30. G. Agelis, N. Tzioumaki, T. Tselios, T. Botić, A. Cencič, and D. Komiotis Eur. J. Med. Chem. 43 2008 1366 1375
31. N. Tzioumaki, E. Tsoukala, S. Manta, G. Agelis, J. Balzarini, and D. Komiotis Arch. Pharm. 342 2009 353 360
32. D.B. Longley, D.P. Harkin, and P.G. Johnston Nat. Rev. Canc. 3 2003 330 338
33. E. Tsoukala, G. Agelis, J. Dolinsek, T. Botić, A. Cencič, and D. Komiotis Bioorg. Med. Chem. 15 2007 3241 3247
34. V. Vanheusden, R. Busson, P. Herdewijn, and S. Van Calenbergh J. Org. Chem. 69 2004 4446 4453
35. J. Milecki, A. Földesi, A. Fischer, R.W. Adamiak, and J. Chattopadhyaya J. Labelled Compd. Rad. 44 2001 763 783
36. M. Bessodes, E. Abushanab, and P.R. Panzica J. Chem. Soc. Chem. Commun. 1981 26 28
37. B.K. Chun, G.Y. Song, and C.K. Chu J. Org. Chem. 66 2001 4852 4858
38. M. Bessodes, D. Komiotis, and K. Antonakis Tetrahedron Lett. 27 1986 579 580
39. J. Herscovici, and K. Antonakis J. Chem. Soc. Chem. Commun. 12 1980 561 564
40. L.S. Jeong, and S.J. Yoo Bioorg. Med. Chem. Lett. 8 1998 847 852
41. R. Van Rijsbergen, M.J.O. Anteunis, and A. De Bruyn J. Carbohydr. Chem. 2 1983 395 404
42. M.J. Kim, L.S. Jeong, J.H. Kim, J.H. Shin, S.Y. Chung, S.K. Lee, and M.W. Chun Nucleosides, Nucleotides Nucleic Acids 23 2004 715 724
43. P.J. Garegg, and B. Samuelsson Synthesis 1979 469 470
44. Z. Liu, B. Classon, and B. Samuelsson J. Org. Chem. 55 1990 4273 4275
45. P.J. Garegg, and B. Samuelsson Synthesis 1979 813 814
46. A.F. Luzzio, and E.M. Menes J. Org. Chem. 59 1994 7267 7272
47. E. De Clercq, J. Balzarini, P.F. Torrence, M.P. Mertes, C.L. Schmidt, D. Shugar, P.J. Barr, A.S. Jones, G. Verhelst, and R.T. Walker Mol. Pharmacol. 19 1981 321 330
48. J. Balzarini, and E. De Clercq Biochim. Biophys. Acta 785 1984 36 45
49. Y. Yamada, H. Yasui, A. Goto, T. Arai, T. Ura, T. Hamaguchi, K. Muro, Y. Shimada, and K. Shirao Int. J. Clin. Oncol. 8 2003 374 380
50. A. Bronckaers, L. Aguado, A. Negri, M.J. Camarasa, J. Balzarini, M.J. Pérez-Pérez, F. Gago, and S. Liekens Biochem. Pharmacol. 78 2009 231 240
51. T.P. Roosild, S. Castronovo, M. Fabbiani, and G. Pizzorno BMC Struct. Biol. 9 2009 14
52. S. Liekens, A. Bronckaers, and J. Balzarini Lancet Oncol. 10 2009 628 635