Organocatalytic synthesis of novel purine and pyrimidine acyclic nucleosides

Tetrahedron Letters

Volumn 53, Issue 50, 2012, Pages 6797-6800

  Palazzolo, Martín A ^a,b   Pérez Sánchez, María ^a   Iribarren, Adolfo M ^b   Lewkowicz, Elizabeth S ^b   Domínguez De María, Pablo ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b UNIVERSIDAD NACIONAL DE QUILMES   (Argentina)

Author keywords

Acyclic nucleosides; Organocatalysis; Phosphonate; Piperazine; Pyrrolidine

Indexed keywords

ACETONE; ACICLOVIR; ACYCLIC NUCLEOSIDE; ALDEHYDE; AMINE; CIDOFOVIR; KETONE; NUCLEIC ACID BASE; PENCICLOVIR; PHOSPHONIC ACID DERIVATIVE; PIPERAZINE DERIVATIVE; PURINE NUCLEOSIDE DERIVATIVE; PYRIMIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SILICON DIOXIDE; TENOFOVIR DISOPROXIL;

ARTICLE; CATALYSIS; CHEMICAL BOND; DRUG SYNTHESIS;

EID: 84868604925     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.10.009     Document Type: Article

References (34)

1. E. De Clercq Annu. Rev. Pharmacol. Toxicol. 51 2011 1 24
2. E. De Clercq J. Med. Chem. 53 2010 1438 1450
3. E. De Clercq, and H.J. Field J. Br. J. Pharmacol. 147 2006 1 11
4. G.B. Elion, P.A. Furman, J.A. Fyfe, P. de Miranda, L. Beauchamp, and H.J. Schaeffer Proc. Natl. Acad. Sci. U.S.A. 74 1977 5716 5720
5. H.J. Schaeffer, L. Beauchamp, P. de Miranda, G.B. Elion, D.J. Bauer, and P. Collins Nature 272 1978 583 585
6. E. De Clercq, J. Descamps, P. De Somer, and A. Holý Science 200 1978 563 565
7. A. Holý, and A. Chihák Biochem. Pharmacol. 30 1981 2359 2361
8. I. Votruba, A. Holý, and E. De Clercq Acta Virol. 27 1983 273 276
9. Holý, A. Current Protocols Nucleic Acid, Chemistry 2005, 14111-14121.
10. D. D'Alonzo, A. Guaragna, and G. Palumbo Chem. Biodivers. 8 2011 373 413
11. A. Paju, M. Päri, A. Selyutina, E. Zusinaite, A. Merits, T. Pehk, K. Siirde, A.M. Müürisepp, T. Kailas, and M. Lopp Nucleosides Nucleotides Nucleic Acids 29 2010 707 720
12. E. De Clercq, and A. Holý Nature Rev. 4 2005 928 940
13. A. Holý Collect. Czech. Chem. Commun. 40 1975 187 214
14. N. Lougiakis, P. Marakos, N. Poul, and J. Balzarini Chem. Pharm. Bull. 56 2008 775 780
15. E. Ichikawa, and K. Kato Curr. Med. Chem. 8 2003 385 423
16. M. Ferrero, and V. Gotor Chem. Rev. 100 2000 4319 4348
17. I.A. Mikhailopulo Curr. Org. Chem. 11 2007 317 335
18. E.S. Lewkowicz, and A.M. Iribarren Curr. Org. Chem 10 2006 1197 1215
19. R. Médici, A.M. Iribarren, and E.S. Lewkowicz Bioorg. Med. Chem. Lett. 19 2009 4210 4212
20. A. Valino, M. Palazzolo, A.M. Iribarren, and E.S. Lewkowicz Appl. Biochem. Biotechnol. 166 2012 300 308
21. M. Dondoni, and A. Massi Angew. Chem. Int. Ed. 47 2008 4638 4660
22. P. Renzi, and M. Bella Chem. Commun. 48 2012 6881 6896
23. P. Domínguez de María, P. Bracco, L.F. Castelhano, and G. Bargeman ACS Catal. 1 2011 70 75
24. S. Shanmuganathan, L. Greiner, and P. Domínguez de María Tetrahedron Lett. 51 2012 6670 6672
25. G.R. Qu, H.L. Zhang, H.Y. Niu, Z.K. Xué, X.X. Lv, and H.M. Guo Green Chem. 14 2012 1877 1879
26. V. Bisai, A. Bisai, and S. Singh Tetrahedron 68 2012 4541 4580
27. M.T. Doel, A.S. Jones, and N. Taylor Tetrahedron Lett. 10 1969 2285 2288
28. V. Pace, P. Hoyos, L. Castoldi, P. Domínguez de María, and A.R. Alcántara ChemSusChem 5 2012 1369 1379
29. M.C. Long, J.R. King, and E.P. Acosta Curr. HIV/AIDS Rep. 6 2009 43 50
30. E. De Clercq Biochem. Pharmacol. 82 2011 99 109
31. A.S. Ray, and K.I. Hostetler Antiviral Res. 92 2011 277 291
32. A. Holý Curr. Pharm. Res. 9 2003 2567 2592
33. Tenofovir disoproxil fumarate is a component of Truvada® antiviral recently approved by the FDA to reduce the risk of sexually acquired HIV infection. http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm312210. htm (Accessed July 2012).
34. Z.-Q. Xu, Y.-L. Qiu, S. Chokekijchai, H. Mitsuya, and J. Zemlicka J. Med. Chem. 38 1995 875 882