A convenient synthesis of novel pyrimidinyl-5′-nor-1′- homocarbanucleosides based on indanol

Synthesis

Volumn , Issue 20, 2005, Pages 3549-3554

  Fernández, Franco ^a   García Mera, Xerardo ^a   López, Carmen ^a   Morales, Melvin ^a   Rodríguez Borges, José Enrique ^b  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF PORTO   (Portugal)

Author keywords

5 Halopyrimidines; Antiviral; Indan carbanucleosides; Mitsunobu reaction; Nucleophilic substitution

Indexed keywords

ALCOHOLS; AROMATIC COMPOUNDS; REACTION KINETICS; SUBSTITUTION REACTIONS;

5-HALOPYRIMIDINES; ANTIVIRAL; INDAN CARBANUCLEOSIDES; MITSUNOBU REACTION; NUCLEOPHILIC SUBSITUTION;

SYNTHESIS (CHEMICAL);

1 (3 HYDROXY 1 INDANYLMETHYL) 1,2,3,4 TETRAHYDROPYRIMIDINE 2,4 DIONE; 1 (3 HYDROXY 1 INDANYLMETHYL) 5 METHYL 1,2,3,4 TETRAHYDROPYRIMIDINE 2,4 DIONE; 5 BROMO 1 (3 HYDROXY 1 INDANYLMETHYL) 1,2,3,4 TETRAHYDROPYRIMIDINE 2,4 DIONE; ANTIVIRUS AGENT; CHLORINE DERIVATIVE; CYTOSINE; INDANONE DERIVATIVE; MESYLIC ACID; NUCLEOSIDE DERIVATIVE; PYRIMIDINE DERIVATIVE; SUCCINIMIDE DERIVATIVE; THYMINE; UNCLASSIFIED DRUG; URACIL; URACIL DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; COXSACKIE VIRUS B4; CROSS COUPLING REACTION; DRUG SYNTHESIS; HALOGENATION; HERPES SIMPLEX VIRUS 1; HERPES SIMPLEX VIRUS 2; HUMAN; HUMAN CELL; MITSUNOBU REACTION; NONHUMAN; REACTION ANALYSIS; SINDBIS VIRUS; STRUCTURE ACTIVITY RELATION; VACCINIA VIRUS; VESICULAR STOMATITIS VIRUS;

EID: 29744449914     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-918420     Document Type: Article

References (32)

1. For recent reviews, see: (a) Rodriguez, J. B.; Comin, M. J. Mini Rev. Med. Chem. 2003, 5, 95.
2. (b) Schneller, S. W. Curr. Top. Med. Chem. 2002, 2, 1087.
3. (c) Ichikawa, E.; Kato, K. Curr. Med. Chem. 2001, 8, 385.
4. (d) Zhu, X.-F. Nucleosides, Nucleotides Nucleic Acids 2000, 19, 651.
5. (e) Crimmins, M. T. Tetrahedron 1998, 54, 9229.
6. (f) Agrofoglio, L.; Challand, S. R. Acyclic, Carbocyclic and l-Nucleosides; Kluwer Academic: Dordrecht, The Netherlands, 1998.
7. (a) Bricaud, H.; Herdewijn, P.; De Clercq, E. Biochem. Pharmacol. 1983, 3583.
8. (b) Montgomery, J. A. Med. Res. Rev. 1982, 2, 271.
9. Cookson, R.; Dudfield, P.; Newton, R.; Ravenscroft, P.; Scopes, D.; Cameron, J. Eur. J. Med. Chem. Chim. Ther. 1985, 20, 375.
10. Arts, E. J.; Wainberg, M. A. Antimicrob. Agents Chemother. 1996, 40, 527.
11. Vince, R.; Hua, M. J. Med. Chem. 1990, 33, 17.
12. Daluge, S. M.; Martin, M. T.; Sickles, B. R.; Livingston, D. A. Nucleosides, Nucleotides Nucleic Acids 2000, 19, 297.
13. (a) Fernández, F.; García-Mera, X.; Morales, M.; Rodríguez-Borges, J. E.; De Clercq, E. Synthesis 2002, 1084.
14. (b) Yao, S.-W.; López, V. H. C.; Fernández, F.; García-Mera, X.; Morales, M.; Rodríguez-Borges, J. E.; Cordeiro, M. N. D. S. Bioorg. Med. Chem. 2003, 11, 4999.
15. Fernández, F.; García-Mera, X.; Morales, M.; Vilariño, L.; Caamaño, O.; De Clercq, E. Tetrahedron 2004, 60, 9245.
16. Liu, J.; Kolar, C.; Lawson, T. A.; Gmeiner, W. H. J. Org. Chem. 2001, 66, 5655.
17. (a) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571.
18. (b) Fernández, F.; García-Mera, X.; Morales, M.; Rodríguez-Borges, J. E. Synthesis 2001, 239.
19. Barral, K.; Courcambeck, J.; Pèpe, G.; Balzarini, J.; Neyts, J.; De Clercq, E.; Camplo, M. J. Med. Chem. 2005, 48, 450.
20. Russ, P.; Schelling, P.; Scapozza, L.; Folkers, G.; De Clercq, E.; Marquez, V. E. J. Med. Chem. 2003, 46, 5045.
21. Cruickshank, K. A.; Jiricny, J.; Reese, C. B. Tetrahedron Lett. 1984, 25, 681.
22. Borcherding, D. R.; Peet, N. P.; Munson, H. R.; Zhang, H.; Hoffman, P. F.; Bowlin, T. L.; Edwards, C. K. J. Med. Chem. 1996, 39, 2615.
23. (a) Mitsunobu, O. Synthesis 1981, 1.
24. (b) Girard, F.; Lee, M. G.; Agrofoglio, L. A. J. Heterocycl. Chem. 1998, 35, 911.
25. Takahata, H.; Takamatsu, T.; Yamazaki, T. J. Org. Chem. 1989, 54, 4812.
26. (a) Sako, M.; Saito, T.; Kameyama, K.; Hirota, K.; Maki, Y. Synthesis 1987, 829.
27. (b) Srivastavam, P. C.; Nagpal, K. L. Experientia 1970, 26, 220.
28. (a) Awano, H.; Shuto, S.; Baba, M.; Kira, T.; Shigeta, S.; Matsuda, A. Bioorg. Med. Chem. 1994, 4, 367.
29. (b) González-Moa, M. J.; Besada, P.; Teijeira, M.; Terán, C.; Uriarte, E. Synthesis 2004, 543.
30. Prussoff, W. H.; Holmes, W. L.; Welch, A. D. Cancer Res. 1953, 13, 221.
31. Robins, M. J.; Barr, P. J.; Giziewicz, J. Can. J. Chem. 1982, 60, 554.
32. De Clercq, E. In 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.