Synthesis of 4-N-alkyl and ribose-modified AICAR analogues on solid support

Tetrahedron

Volumn 64, Issue 27, 2008, Pages 6475-6481

  Oliviero, Giorgia ^a   Amato, Jussara ^a   Borbone, Nicola ^a   D'Errico, Stefano ^a   Piccialli, Gennaro ^a   Bucci, Enrico ^b   Piccialli, Vincenzo ^a   Mayol, Luciano ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b Bioindustry Park del Canavese   (Italy)

Author keywords

AICAR; Combinatorial chemistry; Nucleoside analogues; Solid phase synthesis

Indexed keywords

2',3' SECORIBOSIDE DERIVATIVE; 5 AMINO 4 IMIDAZOLECARBOXAMIDE RIBOSIDE; 5 AMINOIMIDAZOLE 4 (N)CARBOXAMIDE 1 RIBOSIDE DERIVATIVE; CARBON; INOSINE DERIVATIVE; PURINE; PYRIDINE; RIBOSE;

ALKYLATION; ARTICLE; BREAST CANCER; COLORIMETRY; CONTROLLED STUDY; DRUG DEGRADATION; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SOLID;

EID: 44349156991     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.04.071     Document Type: Article

References (40)

1. In: Chu C.K. (Ed). Antiviral Nucleosides: Chiral Synthesis and Chemotherapy (2003), Elsevier, Amsterdam, The Netherlands
2. Simons C., Wu Q., and Htar T.T. Curr. Top. Med. Chem. 5 (2005) 1191-1203
3. De Clercq E., and Neyts J. Rev. Med. Virol. 14 (2004) 289-300
4. Lagoja I.M. Chem. Biodivers. 2 (2005) 1-50
5. Kimura K., and Bugg T.D.H. Nat. Prod. Rep. 20 (2003) 252-273
6. Rachakonda S., and Cartee L. Curr. Med. Chem. 11 (2004) 775-793
7. Knapp S. Chem. Rev. 95 (1995) 1859-1876
8. Miura S., and Izuta S. Curr. Drug Targets 5 (2004) 191-195
9. Parker W.B., Secrist J.A., and Waud W.R. Curr. Opin. Investig. Drugs 5 (2004) 592-596
10. Szafraniec S.I., Stachnick K.J., and Skierski J.S. Acta Pol. Pharm. 61 (2004) 223-232
11. Gandhi V., Keating M.J., Bate G., and Kirkpatrick P. Nat. Rev. Drug Discov. 5 (2006) 17-18
12. Matthews S.J. Clin. Ther. 28 (2006) 184-203
13. Pui C.H., Jeha S., and Kirkpatrick P.C. Nat. Rev. Drug Discov. 4 (2005) 369-370
14. Kaminskas E., Farrell A., Abraham S., Baird A., Hsieh L.S., Lee S.L., Leighton J.K., Patel H., Rahman A., Shidhara R., Wang Y.C., and Pazdur R. Clin. Cancer Res. 11 (2005) 3604-3608
15. Rutter G.A., Silva Xavier G., and Lecler I. Biochem. J. 375 (2003) 1-16
16. Gaidhu M.P., Fediuc S., and Ceddia R.B. J. Biol. Chem. 281 (2006) 25956-25964
17. Frank R.N. Am. J. Ophthalmol. 133 (2002) 693-698
18. Lara D.R., Dall'Igna O.P., Ghisolfi E.S., and Brunstein M.G. Prog. Neuropsychopharmacol. Biol. Psychiatry 30 (2006) 617-629
19. Kohyama N., Katashima T., and Yamamoto Y. Synthesis 17 (2004) 2799-2804
20. Ulrich S.M., Sallee N.A., and Shokat K.M. Bioorg. Med. Chem. Lett. 12 (2002) 3223-3227
21. Wall M., Shim J.H., and Benkovic S.J. Biochemistry 39 (2000) 11303-11311
22. Minakawa N., Kojima N., Sasaki T., and Matsuda A. Nucleosides Nucleotides 15 (1996) 251-263
23. Minakawa N., Takeda T., Sasaki T., Matsuda A., and Ueda T. J. Med. Chem. 34 (1991) 778-786
24. Mizuno A., Tsujino M., Takada M., Hayashi M., and Atsumi K. J. Antibiot. (Tokyo) 27 (1974) 775-782
25. Kamata K., Okubo M., Ishigamori E., Masaki Y., Uchida H., Watanabe K., and Kashiwagi N. Transplantation 35 (1983) 144-149
26. Sidwell R.W., Huffman J.H., Khare G.P., Allen L.B., Witkowski J.T., and Robins R.K. Science 177 (1972) 705-706
27. Guezguez R., Bougrin K., El Akri K., and Benhida R. Tetrahedron Lett. 47 (2006) 4807-4811
28. Kalman T.I., and Houston D.M. Nucleosides Nucleotides 8 (1989) 899-902
29. Oliviero G., Amato J., Borbone N., D'Errico S., Piccialli G., and Mayol L. Tetrahedron Lett. 48 (2007) 397-400
30. De Napoli L., Messere A., Montesarchio D., Piccialli G., and Varra M. J. Chem. Soc., Perkin Trans. 1 (1997) 2079-2082
31. Fujii T., Saito T., Risata H., and Shinbo K. Chem. Pharm. Bull. 38 (1990) 3326-3330
32. Casanova E., Hernàndez A.I., Priego E.M., Liekens S., Camarasa M.J., Balzarini J., and Pérez-Pérez M.J. J. Med. Chem. 49 (2006) 5562-5570
33. De Napoli L., Messere A., Montesarchio D., and Piccialli G. J. Org. Chem. 60 (1995) 2251-2253
34. Fukuoka M., Shuto S., Minakawa N., Ueno Y., and Matsuda A. J. Org. Chem. 65 (2000) 5238-5248
35. For general accounts on lead tetraacetate reactions, see:
36. Criegee R. In: Wiberg K.B. (Ed). Oxidation in Organic Chemistry (1965), Academic, New York, NY Part A
37. Sheldon R.A., and Kochi J.K. Org. React. 19 (1972) 279-421
38. Mihailovic M.L., Cekovic Z., and Lorenc L. In: Mijs W.J., and De Jonge C.R.H.I. (Eds). Organic Synthesis by Oxidation with Metal Compounds (1986), Plenum, New York, NY 741-816
39. Hussain R.F., Nouri A.M., and Oliver R.T. J. Immunol. Methods 15 (1993) 86-89
40. Shaw E. J. Am. Chem. Soc. 80 (1958) 3899-3902