Synthesis and biological evaluation of diastereoisomerically pure N,O-nucleosides

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 19, 2010, Pages 6970-6976

  Bortolini, Olga ^a   Nino, Antonio De ^a   Eliseo, Tommaso ^b   Gavioli, Riccardo ^c   Maiuolo, Loredana ^a   Russo, Beatrice ^a   Sforza, Fabio ^c  

^a UNIVERSITY OF CALABRIA   (Italy)

^b UNIVERSITY OF ROME TOR VERGATA   (Italy)

^c UNIVERSITY OF FERRARA   (Italy)

Author keywords

1,3 Dipolar cycloaddition; Cytotoxic activity; N,O Nucleosides

Indexed keywords

CIS 4' AZA 4' (N METHYL) 3' 4 HYDROXYPHENYL 2',3' DIDEOXYTHYMIDINE; CIS 4' AZA 4' (N METHYL) 3' 4 NITROPHENYL 2',3' DIDEOXYTHYMIDINE; CIS 4' AZA 4' (N METHYL) 3' O CHLOROPHENYL 2',3' DIDEOXYTHYMIDINE; CIS 4' AZA 4' (N METHYL) 3' O HYDROXYPHENYL 2',3' DIDEOXYTHYMIDINE; CIS 4' AZA 4' (N METHYL) 3' PHENYL 2',3' DIDEOXYCYTIDINE; CIS 4' AZA 4' (N TERT BUTYL) 3' FURYL 2',3' DIDEOXYADENOSINE; CIS 4' AZA 4' (N TERT BUTYL) 3' FURYL 2',3' DIDEOXYTHYMIDINE; CIS 4' AZA 4' (N TERT BUTYL) 3' PHENYL 2',3' DIDEOXY 5 FLUOROURIDINE; CIS 4' AZA 4' (N TERT BUTYL) 3' PHENYL 2',3' DIDEOXYADENOSINE; CIS 4' AZA 4' (N TERT BUTYL) 3' PHENYL 2',3' DIDEOXYCYTIDINE; CIS 4' AZA 4' (N TERT BUTYL) 3' PHENYL 2',3' DIDEOXYTHYMIDINE; CIS 4' AZA 4' (N TERT BUTYL) 3' PHENYL 2',3' DIDEOXYURIDINE; NITRONE; NUCLEOSIDE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CELL LINE; CELL PROLIFERATION; CYCLIZATION; DRUG CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; LEUKEMIA CELL LINE; LYMPHOBLASTOID CELL LINE; STEREOCHEMISTRY;

ANTINEOPLASTIC AGENTS; APOPTOSIS; B-LYMPHOCYTES; CELL LINE; CELL PROLIFERATION; CYCLIZATION; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; JURKAT CELLS; MOLECULAR STRUCTURE; NUCLEOSIDES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77956650091     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.08.024     Document Type: Article

References (39)

1. H. Choo, X. Chen, V. Yadav, J. Wang, R.F. Schinazi, and C.K. Chu J. Med. Chem. 49 2006 1635
2. U. Chiacchio, A. Corsaro, D. Iannazzo, A. Piperno, V. Pistar, A. Rescifina, R. Romeo, V. Valveri, A. Mastino, and G. Romeo J. Med. Chem. 46 2003 3696
3. Y.-S. Lee, and K.B. Hyean Bioorg. Med. Chem. Lett. 12 2002 1395
4. E. De Clercq Med. Res. Rev. 22 2002 531
5. P. Merino, S. Franco, F.L. Merchan, and T. Tejero Recent Res. Dev. Org. Chem. 4 2000 227
6. M. Tsuda, K. Hirano, T. Kubota, and J. Kobayashi Tetrahedron Lett. 40 1999 4819
7. H. Imamura Chem. Pharm. Bull. 8 1960 449
8. R. Singh, S. Singh Bhella, A.K. Sexana, M. Shanmugavel, A. Faruka, and M.P.S. Ishar Tetrahedron 63 2007 2283
9. U. Chiacchio, A. Padwa, and G. Romeo Curr. Org. Chem. 13 2009 422 and references cited therein
10. U. Chiacchio, E. Balestrieri, B. Macchi, D. Iannazzo, A. Piperno, A. Rescifina, R. Romeo, M. Saglimbeni, M.T. Sciortino, V. Valveri, A. Mastino, and G. Romeo J. Med. Chem. 48 2005 1389
11. U. Chiacchio, A. Rescifina, D. Iannazzo, A. Piperno, R. Romeo, L. Borrello, M.T. Sciortino, E. Balestrieri, B. Macchi, A. Mastino, and G. Romeo J. Med. Chem. 50 2007 3747
12. M. Fredrickson Tetrahedron 53 1997 403
13. R.C.F. Jones A. Padwa, W.H. Pearson, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products Vol. 59 2002 Wiley New York 1 82
14. J.D. Morrison Asymmetric Synthesis Vol. 1 1983 Academic Press New York
15. J. Mulzer, H.-J. Altenbach, M. Brauun, K. Krohn, and H.-U. Reissing Organic Synthesis Highlights 1991 VCH New York 77
16. A. Padwa B.M. Trost, I. Fleming, Comprehensive Organic Synthesis Vol. 4 1991 Pergamon Oxford 1069
17. K.B. Simonsen, P. Bayón, R.G. Hazell, K.V. Gothelf, and K.A. Jørgensen J. Am. Chem. Soc. 121 1999 3845
18. L.R. Domingo Eur. J. Org. Chem. 2000 2265
19. P. Merino, J. Revuelta, T. Tejero, U. Chiacchio, A. Rescifina, and G. Romeo Tetrahedron 59 2003 3581
20. P. DeShong, C.M. Dicken, R.R. Staib, A.J. Freyer, and S.M. Weinreb J. Org. Chem. 47 1982 4397
21. O. Bortolini, A. De Nino, L. Maiuolo, B. Russo, G. Sindona, and A. Tocci Tetrahedron Lett. 48 2007 7125
22. O. Bortolini, M. D'Agostino, A. De Nino, L. Maiuolo, M. Nardi, and G. Sindona Tetrahedron 64 2008 8078
23. C.R. Strauss, and R.S. Varma Top. Curr. Chem. 266 2006 199
24. M.M. Andrade, M.T. Barros, and R.C. Pinto Tetrahedron 64 2008 10521
25. M.M. Andrade, M.T. Barros, and R.C. Pinto Synth. Commun. 40 2010 855
26. G.T. Balogh, K. Vukics, A. Könczöl, A. Kis-Varga, A. Gere, and J. Fischer Bioorg. Med. Chem. Lett. 15 2005 3012
27. A. Dhainaut, A. Tizot, E. Raimbaud, B. Lockhart, P. Lestage, and S. Goldstein J. Med. Chem. 43 2000 2165
28. S. Kim, G.V.M.D. Vilela, J. Bouajila, A.G. Dias, F.Z.G.A. Cyrino, E. Bouskela, P.R.R. Costa, and F. Nepveu Bioorg. Med. Chem. 15 2007 3572
29. IUPAC Compendium of Chemical Terminology; 2nd ed.; 1997. Available from: < http://www.iupac.org/publications/compendium/index.html >.
30. A. Archelas, and R. Furstoss J. Org. Chem. 64 1999 6112
31. G.P.G. Grant, A. Popova, and P.Z. Qin Biochem. Biophys. Res. Commun. 371 2008 451
32. T.J. Bloom, and J.A. Beavo Proc. Natl. Acad. Sci. 93 1996 14188
33. F. Praz, and P. Lesavre J. Immunol. 131 1983 1396
34. B. Bastin, M.D. Payet, and G. Dupuis Cell Immunol. 128 1990 385
35. F. Micheletti, R. Guerrini, A. Formentin, A. Canella, M. Marastoni, M. Bazzaro, R. Tomatis, S. Traniello, and R. Gavioli Eur. J. Immunol. 29 1999 2579
36. F.M. Cordero, M. Salvati, F. Pisaneschi, and A. Brandi Eur. J. Org. Chem. 2004 2205
37. R. Dalpozzo, A. De Nino, L. Maiuolo, A. Procopio, R. Romeo, and G. Sindona Synthesis 2002 172
38. F. Denizot, and R. Lang J. Immunol. Methods 22 1986 271
39. P. Bergamini, and R. Gavioli Inorg. Chem. 46 2007 4267