Synthesis of [60]fullerene-glycopyranosylaminopyrimidin-4-one conjugates

Tetrahedron

Volumn 64, Issue 19, 2008, Pages 4427-4437

  Jordão, Carina I C ^a   Farinha, Andreia S F ^a   Enes, Roger F ^a   Tomé, Augusto C ^a   Silva, Artur M S ^a   Cavaleiro, José A S ^a   Ramos, Catarina I V ^a   Santana Marques, M G ^a   Almeida Paz, Filipe A ^b   de la Torre Ramirez, José M ^c   de la Torre, Maria D L ^c   Nogueras, Manuel ^c  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b UNIVERSITY OF AVEIRO   (Portugal)

^c UNIVERSITY OF JAÉN   (Spain)

Author keywords

Fullerene derivatives; Mass spectrometry; Nucleosides; X ray crystallography

Indexed keywords

AZOMETHINE YLIDE; CARBON; FULLERENE DERIVATIVE; GLYCOPYRANOSIDE; PYRIMIDINE DERIVATIVE; SARCOSINE; URIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CONJUGATION; CYCLOADDITION; CYCLOPROPANATION; ESTERIFICATION; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 41549138648     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.057     Document Type: Article

References (59)

1. Recent reviews:
2. Bendikov M., Wudl F., and Perepichka D.F. Chem. Rev. 104 (2004) 4891-4945
3. Sánchez L., Herranz A., and Martín N. J. Mater. Chem. 15 (2005) 1409-1421
4. Martín N. Chem. Commun. (2006) 2093-2104
5. Figueira-Duarte T.M., Gégout A., and Nierengarten J.-F. Chem. Commun. (2007) 109-119
6. In: Langa F., and Nierengarten J.-F. (Eds). Fullerenes: Principles and Applications (2007), RSC, Cambridge, UK
7. Reviews:
8. Jensen W., Wilson S.R., and Schuster D.I. Bioorg. Med. Chem. 4 (1996) 767-779
9. Da Ros T., and Prato M. Chem. Commun. (1999) 663-669
10. Tagmatarchis N., and Shinohara H. Mini-Rev. Med. Chem. 1 (2001) 339-348
11. Nakamura E., and Isobe H. Acc. Chem. Res. 36 (2003) 807-815
12. Bosi S., Da Ros T., Spalluto G., and Prato M. Eur. J. Med. Chem. 38 (2003) 913-923
13. Bianco A., and Da Ros T. Biological Applications of Fullerenes. In: Langa F., and Nierengarten J.-F. (Eds). Fullerenes: Principles and Applications (2007), RSC, Cambridge, UK
14. Recent articles:
15. Zakharian T.Y., Seryshev A., Sitharaman B., Gilbert B.E., Knight V., and Wilson L.J. J. Am. Chem. Soc. 127 (2005) 12508-12509
16. Ashcroft J.M., Tsyboulski D.A., Hartman K.B., Zakharian T.Y., Marks J.W., Weisman R.B., Rosenblumb M.G., and Wilson L.J. Chem. Commun. (2006) 3004-3006
17. Troshina O.A., Troshin P.A., Peregudov A.S., Kozlovskiy V.I., Balzarini J., and Lyubovskaya R.N. Org. Biomol. Chem. 5 (2007) 2783-2791
18. Liu J., Ohta S., Sonoda A., Yamada M., Yamamoto M., Nitta N., Murata K., and Tabata Y. J. Controlled Release 117 (2007) 104-110
19. Enes R.F., Tomé A.C., Cavaleiro J.A.S., Amorati R., Fumo M.G., Pedulli G.F., and Valgimigli L. Chem.-Eur. J. 12 (2006) 4646-4653
20. Enes R.F., Tomé A.C., Cavaleiro J.A.S., El-Agamey A., and McGarvey D.J. Tetrahedron 61 (2005) 11873-11881
21. Enes R.F., Tomé A.C., and Cavaleiro J.A.S. Tetrahedron 61 (2005) 1423-1431
22. De la Torre M.D.L., Rodrigues A.G.P., Tomé A.C., Silva A.M.S., and Cavaleiro J.A.S. Tetrahedron 60 (2004) 3581-3592
23. Negrillo J., Nogueras M., Sanchéz A., and Melgarejo M. Chem. Pharm. Bull. 36 (1988) 386-393
24. Nogueras M., Cobo J., Quijano M.L., Melguizo M., Sanchez A., and Melgarejo M. Nucleosides Nucleotides 13 (1994) 447-457
25. Ungurenasu C., Pinteala M., and Simionescu B.C. Synthesis (2005) 361-363
26. Greisch J.-F., and Pauw E.D. J. Mass Spectrom. 42 (2007) 304-311
27. Sessler J.L., Jayawickramarajah J., Gouloumis A., Torres T., Guldi D.M., Maldonado S., and Stevenson K.J. Chem. Commun. (2005) 1892-1894
28. Torres T., Gouloumis A., Sanchez-Garcia D., Jayawickramarajah J., Seitz W., Guldi D.M., and Sessler J.L. Chem. Commun. (2007) 292-294
29. Maggini M., Scorrano G., and Prato M. J. Am. Chem. Soc. 115 (1993) 9798-9799
30. 1H NMR discussion, protons H-5 were indicated as H-5a (the one with a cis relationship with proton H-2) and H-5b.
31. Laprévote O., Ducrot P., Thal C., Serani L., and Das B.P. J. Mass Spectrom. 31 (1996) 1149-1155
32. Madhusudanam K.P. J. Mass Spectrom. 41 (2006) 1096-1104
33. Tsunematsu H., Ikeda H., Hanazono H., Inagaki M., Isobe R., Higuchi R., Goto Y., and Yamamoto M. J. Mass Spectrom. 38 (2003) 188-195
34. Gaucher S.P., and Leary J.A. Anal. Chem. 70 (1998) 3009-3014
35. Perreault H., and Costello C.E. J. Mass Spectrom. 34 (1999) 184-197
36. Zhu X., and Sato T. Rapid Commun. Mass Spectrom. 21 (2007) 191-198
37. Allen F.H. Acta Crystallogr., Sect. B 58 (2002) 380-388
38. Allen F.H., and Motherwell W.D.S. Acta Crystallogr., Sect. B 58 (2002) 407-422
39. Ferguson G., Low J.N., Nogueras M., Cobo J., Lopez M.D., Quijano M.L., and Sanchez A. Acta Crystallogr., Sect. C 54 (1998) IUC9800031 10.1107/S0108270198099521
40. Cobo J., Melguizo M., Sanchez A., Nogueras M., Low J.N., and Ferguson G. Acta Crystallogr., Sect. C 52 (1996) 148-150
41. Cremer D., and Pople J.A. J. Am. Chem. Soc. 97 (1975) 1354-1358
42. Bernstein J., Davis R.E., Shimoni L., and Chang N.L. Angew. Chem., Int. Ed. Engl. 34 (1995) 1555-1573
43. Levene P.A., and Tipson R.S. J. Biol. Chem. 106 (1934) 113-124
44. Scheit K.H. Chem. Ber. 99 (1966) 3884-3891
45. Fromageot H.P.M., Grieffin B.E., Reese C.B., and Sulston J.E. Tetrahedron 23 (1967) 2315-2331
46. Bingel C. Chem. Ber. 126 (1993) 1957-1959
47. Bradshaw T.K., and Hutchinson D.W. Chem. Soc. Rev. 6 (1977) 43-62
48. Kottke T., and Stalke D. J. Appl. Crystallogr. 26 (1993) 615-619
49. APEX2. Data Collection Software Version 2.1-RC13 (2006), Bruker AXS, Delft, The Netherlands
50. Cryopad. Remote Monitoring and Control, Version 1.451 (2006), Oxford Cryosystems, Oxford, United Kingdom
51. © (1997-2005), Bruker AXS, Madison, Wisconsin, USA
52. Sheldrick G.M. SADABS v.2.01, Bruker/Siemens Area Detector Absorption Correction Program (1998), Bruker AXS, Madison, Wisconsin, USA
53. Sheldrick G.M. SHELXS-97, Program for Crystal Structure Solution (1997), University of Göttingen, Göttingen, Germany
54. Sheldrick G.M. SHELXL-97, Program for Crystal Structure Refinement (1997), University of Göttingen, Göttingen, Germany
55. van der Sluis P., and Spek A.L. Acta Crystallogr., Sect. A 46 (1990) 194-201
56. Spek A.L. Acta Crystallogr., Sect. A 46 (1990) C34
57. Spek A.L. PLATON, A Multipurpose Crystallographic Tool (2003), Utrecht University, Utrecht, The Netherlands
58. Flack H.D., and Bernardinelli G. J. Appl. Crystallogr. 33 (2000) 1143-1148
59. Flack H.D. Acta Crystallogr., Sect. A 39 (1983) 876-881