Synthesis and antiviral activities of novel purinyl- and pyrimidinyl-carbanucleosides derived from indan

Synthesis

Volumn , Issue 12, 2008, Pages 1845-1852

  Alonso, Nerea ^a   Caamaño, Olga ^a   Fernández, Franco ^a   García Mera, Xerardo ^a   Morales, Melvin ^a   Rodríguez Borges, José Enrique ^b   De Clercq, Eric ^c  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF PORTO   (Portugal)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Antiviral activity; Indan carbanucleosides; Mitsunobu reaction; Suzuki Miyaura reaction; Synthesis

Indexed keywords

ADDITION REACTIONS; DERIVATIVES; HEALTH; METHANOL;

(I ,J) CONDITIONS; ANTIVIRAL ACTIVITIES; ARYL BORONIC ACIDS; COU PLING REACTIONS; HYDROXY METHYL; INDANOL; NUCLEOSIDE DERIVATIVES; SUZUKI-MIYAURA REACTIONS; SYNTHESIS (OF CHIRAL IONIC LIQUIDS);

REACTION KINETICS;

3 HYDROXYMETHYL 1 INDANOL; ABACAVIR; BORONIC ACID DERIVATIVE; CARBOVIR; INDAN CARBANUCLEOSIDE; INDAN DERIVATIVE; NUCLEOSIDE DERIVATIVE; SUCCINIMIDE DERIVATIVE;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CONTROLLED STUDY; COXSACKIE VIRUS B4; CROSS COUPLING REACTION; CYTOMEGALOVIRUS; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; MITSUNOBU REACTION; NONHUMAN; PARAINFLUENZA VIRUS 3; SINDBIS VIRUS; SUZUKI MIYAURA REACTION; VACCINIA VIRUS; VARICELLA ZOSTER VIRUS; VERO CELL; VESICULAR STOMATITIS VIRUS;

EID: 46649118297     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067091     Document Type: Article

References (42)

1. Part of this work was presented at the XIV Congreso Nacional of The Sociedad Española de Química Terapéutica, Bilbao: Spain, September 2005.
2. For recent reviews on carbanucleosides, see: (a) Rodríguez. J. B.; Comin, M. J. Mini-Rev. Med. Chem. 2003, 3, 95.
3. Ichikawa, E.; Kato, K. Curr. Top. Med. Chem. 2001, 8, 385.
4. Zhu, X.-F. Nucleosides, Nucleotides Nucleic Acids 2000, 19, 651.
5. Ferrero, M.; Gotor, V. Chem. Rev. 2000, 100, 4319.
6. Agrofoglio, L.; Challand, S. R. Acyclic, Carbocyclic and L-Nucleosides; Kluwer Academic: Dordrecht, 1998.
7. (a) Roberts, S.; Biggadike, K.; Borthwick, A. D.; Kirk, B. Topics in Medicinal Chemistry; Leeming, P. R., Ed.; Royal Society of Chemistry: London, 1988.
8. Marquez, V. E.; Lim, M. Med. Res. Rev. 1986, 6, 1.
9. Saunders, J.; Cameron, J. M. Med. Res. Rev. 1995, 15, 497.
10. (a) Vince, R.; Hua, M.; Brownell, J.; Daluge, S.; Lee, F.; Shannon, W. M.; Lavelle, G. C.; Quails, J.; Weislow, O. S.; Kiser, R.; Canonico, P. G.; Schultz, R. H.; Narayanan, V. L.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Biochem. Biophys. Res. Commun. 1988, 156, 1046.
11. Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17.
12. Vince, R.; Peterson, M. L.; Lackey, J. W.; Mook, R. A.; Partridge, J. J. PCT Int. Appl. WO 9115490, 1991;
13. Chem. Abstr. 1992, 116, 59910.
14. (a) Daluge, S. M.; Good, S. S.; Faleto, M. B.; Miller, W. H.; St. Clair, M. H.; Boone, L. R.; Tisdale, M.; Parry, N. R.; Reardon, J. E.; Dornsife, R. E.; Averett, D. R.; Krenitsky, T. A. Antimicrob. Agents Chemother. 1997, 41, 1082.
15. Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192.
16. Foster, R. H.; Faulds, D. Drugs 1998, 55, 729.
17. (a) Fernández, F.; García-Mera, X.; Morales, M.; Rodriguez-Borges, J. E.; De Clercq, E. Synthesis 2002, 1084.
18. Yao, S.-W.; Lopez, V. H. C.; Fernández, F.; Garcia-Mera, X.; Morales, M.; Rodriguez-Borges, J. E.; Cordeiro, M. N. D. S. Bioorg. Med. Chem. 2003, 11, 4999.
19. (a) Fernández, F.; García-Mera, X.; Morales, M.; Vilariño, L.; Caamaño, O.; De Clercq, E. Tetrahedron 2004, 60, 9245.
20. Fernández, F.; García-Mera, X.; López, C.; Morales, M.; Rodríguez-Borges, J. E. Synthesis 2005, 3549.
21. Thomas, S.; McDowall, J. E.; Cheah, V.; Bye, A.; Segal, M. B. The Entry of Abacavir into the Guinea-Pig Brain: Comparison with other Reverse Transcriptase Inhibitors: 12th World AIDS Conference: Geneva, 1998.
22. (a) Cheson, B. D. Hematol. Cell. Ther. 1996, 38 (Suppl. 2), 109.
23. Bergmann, L. Leukemia 1997, 11 (Suppl. 2), 29.
24. Hocek, M.; Hol, A.; Votruba, I.; Dvoráková, H. J. Med. Chem. 2000, 43, 1817.
25. Grunewald, G. L.; Sall, D. J.; Monn, J. A. J. Med. Chem. 1988, 31, 433.
26. Fernández, F.; García-Mera, X.; Rodriguez-Borges, J. E. Tetrahedron: Asymmetry 2001, 12, 365.
27. (a) Mitsunobu, O. Synthesis 1981, 1.
28. Hughes, D. L. Org. React. 1992, 42, 335.
29. Lawrence, S. PharmaChem 2002, 1, 12.
30. But, T. Y. S.; Toy, P. H. Chem. Asian J. 2007, 2, 1340.
31. (a) Hocek, M. Ear. J. Org. Chem. 2003, 245.
32. Havelková, M.; Dvorák, D.; Hocek, M. Synthesis 2001, 1704.
33. Havelková, M.; Hocek, M.; Cesnek, M.; Dvorák, D. Synlett 1999, 1145.
34. (a) Hocek, M. Eur. J. Org. Chem. 2003, 245.
35. Hocek, H.; Hockova. D.; Stambasky, J. Collect. Czech. Chem. Commun. 2003, 68, 837.
36. Hocek, H.; Holy, A.; Votruba, I.; Dvorakova, H. J. Med. Chem. 2000, 43, 1817.
37. Havelková, M.; Hocek, M.; Cesnek, M.; Dvorák, D. Synlett 1999, 1145.
38. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
39. Fernández, F.; García-Mera, X.; Morales, M.; Rodríguez-Borges, J. E. Synthesis 2001, 239.
40. (a) Sako, M.; Saito, T.; Kameyama, K.; Hirota, K.; Maki, Y. Synthesis 1987, 829.
41. Srivastavam, P. C.; Nagpal, K. L. Experientia 1970, 26, 220.
42. De Clercq, E. In Vivo and Ex Vivo Text Systems to Rationalize Drug Design and Delivery; Cromelin, D.; Couvreur, P.; Duchene, D., Eds.; Editions de Santé: Paris, 1994.