Rapid access to acyclic nucleosides via conjugate addition

Tetrahedron

Volumn 59, Issue 12, 2003, Pages 2177-2184

  Guillarme, Stéphane ^a   Legoupy, Stéphanie ^a   Aubertin, Anne Marie ^b   Olicard, Cécile ^c   Bourgougnon, Nathalie ^c   Huet, François ^a  

^a UNIVERSITÉ DU MAINE   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

^c Centre de Recherche et d'Enseignement Yves Coppens   (France)

Author keywords

Acyclic nucleosides; Analogs of penciclovir; Deaza purine and deaza pyrimidine; Michael addition

Indexed keywords

ACICLOVIR; ACYCLIC NUCLEOSIDE; DIETHYLMETHYLENEMALONATE; GANCICLOVIR; PENCICLOVIR; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CONJUGATION; DRUG SYNTHESIS; INFRARED SPECTROSCOPY; MICHAEL ADDITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037450978     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00190-X     Document Type: Article

References (26)

1. Agrofoglio L.A., Challand S.R. Acyclic, Carbocyclic and L-Nucleosides. 1998;Kluwer Academic, Dordrecht. pp 18-173.
2. (a) Elion G.B., Furman P.A., De Miranda P., Beauchamp L., Schaeffer H.J. Proc. Natl Acad. Sci. USA. 74:1977;5716
3. (b) Schaeffer H.J., Beauchamp L., De Miranda P., Elion G.B., Bauer D.J., Collins P. Nature. 272:1978;583
4. (c) Schaeffer, H. J. US Patent 4360522, 1982; Chem. Abstr. 1980, 93, 186414.
5. (a) Martin J.C., Dvorak C.A., Smee D.F., Matthews T.R., Verheyden J.P.H. J. Med. Chem. 26:1983;759
6. (b) Fan-Havard P., Nahata M.C., Brady M.T. J. Clin. Pharm. Ther. 75:1989;329
7. (c) Faulds D., Heel R.C. Drugs. 39:1990;597.
8. (a) Prandit U.K., Grose W.F., Eggelte R.A. Synth. Commun. 2:1972;345
9. (b) Harnden M.R., Jarvest R.L., Bacon T.H., Boyd M.R. J. Med. Chem. 30:1987;1636
10. (c) Johansson, K. N. G.; Lindborg, B. G.; Noren, J. O. Eur. Pat. Appl. EP 84-850390, December 13, 1984.
11. (a) Lira E.P., Huffman C.W. J. Org. Chem. 31:1966;2188
12. (b) Scheiner P., Geer A., Bucknor A.-M., Imbach J.-L., Schinazi R.F. J. Med. Chem. 32:1989;73
13. (c) Geen G.R., Kincey P.M. Tetrahedron Lett. 33:1992;4609
14. (d) Lazrek H.B., Khaïder H., Rochdi A., Barascut J.-L., Imbach J.-L. Tetrahedron Lett. 37:1996;4701
15. (e) Esposito A., Perino M.G., Taddei M. Eur. J. Org. Chem. 1999;931.
16. (a) Legraverend M., Nia Ngongo-Tekam R.-M., Bisagni E., Zerial A. J. Med. Chem. 10:1967;665
17. (b) Montgomery J.A., Johanssan G. Tetrahedron. 42:1986;6541
18. (c) Pecquet P., Huet F., Legraverend M., Bisagni E. Heterocycles. 34:1992;739.
19. Delépine J.-L., Pecquet P., Betton M.-C., Huet F. Synth. Commun. 26:1996;2819.
20. Baizer M.M., Clark J.R., Dub M., Loter A. J. Org. Chem. 21:1956;1276.
21. Zou R., Robins M.J. Can. J. Chem. 65:1987;1436.
22. Alexandre, F.-R. PhD Thesis, Université du Maine, 1999.
23. Zhou J., Shevlin P.B. Synth. Commun. 27:1997;3591.
24. Byun H.-S., Reddy K.C., Bittman R. Tetrahedron Lett. 35:1994;1371.
25. An alternetive way for synthesis of 5b is a substitution: Marcuccio, S. M.; Jarvis, K. E. Int. Pat. Appl. WO 9912927, March 18, 1999.
26. Chen, S.-F.; Windle, B. E.; Fletcher, T. M.; Maine, I.; Kerwin, S. M.; Salazar, M.; Mamiga, B.; Wajima, M. Int. Pat. Appl. WO 9702279, January 23, 1997.