A new method for the synthesis of 2-glycosylamino pyridines

Tetrahedron

Volumn 52, Issue 16, 1996, Pages 5845-5856

  Cobo, Justo ^a   Melguizo, Manuel ^a   Sánchez, Adolfo ^a   Nogueras, Manuel ^a   De Clercq, Erik ^b  

^a UNIVERSITY OF JAÉN   (Spain)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE DERIVATIVE; PYRIDINE DERIVATIVE;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0029940959     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00214-1     Document Type: Article

References (15)

1. Previously published: Cobo, J.; Melguizo, M.; Sánchez, A.; Nogueras, M., Synlett, 1993, 4, 297.
2. Cobo, J.; García, C.; Melguizo, M.: Sánchez, A.; Nogueras, M., Tetrahedron, 1994, 50, 10345.
3. Strazewski, P.; Tamm, C., Angew, Chem., 1990, 102, 37; Angew. Chem. Int. Ed. Engl., 1990, 29, 36. Seela, F.; Gumbiowski, R., Helv. Chim. Acta, 1991, 74, 1048. Cristalli, G.; Vittori, S.; Eleuteri, A.; Grifantini, M.; Volpini, R.; Lupidi, G.; Capolongo, L.; Pesenti, E., J. Med. Chem., 1991, 34, 2226.
4. Strazewski, P.; Tamm, C., Angew, Chem., 1990, 102, 37; Angew. Chem. Int. Ed. Engl., 1990, 29, 36. Seela, F.; Gumbiowski, R., Helv. Chim. Acta, 1991, 74, 1048. Cristalli, G.; Vittori, S.; Eleuteri, A.; Grifantini, M.; Volpini, R.; Lupidi, G.; Capolongo, L.; Pesenti, E., J. Med. Chem., 1991, 34, 2226.
5. Strazewski, P.; Tamm, C., Angew, Chem., 1990, 102, 37; Angew. Chem. Int. Ed. Engl., 1990, 29, 36. Seela, F.; Gumbiowski, R., Helv. Chim. Acta, 1991, 74, 1048. Cristalli, G.; Vittori, S.; Eleuteri, A.; Grifantini, M.; Volpini, R.; Lupidi, G.; Capolongo, L.; Pesenti, E., J. Med. Chem., 1991, 34, 2226.
6. Strazewski, P.; Tamm, C., Angew, Chem., 1990, 102, 37; Angew. Chem. Int. Ed. Engl., 1990, 29, 36. Seela, F.; Gumbiowski, R., Helv. Chim. Acta, 1991, 74, 1048. Cristalli, G.; Vittori, S.; Eleuteri, A.; Grifantini, M.; Volpini, R.; Lupidi, G.; Capolongo, L.; Pesenti, E., J. Med. Chem., 1991, 34, 2226.
7. Purification from the crude reaction of the compounds 4a-d were also carried out through crystallization from methanol (molar ratio 2:3 used in these cases were 1.5:1). Yields of 4a-d by crytallization were between 60-75. This permits one to use a larger amount of starting compound.
8. Asenjo, R.; Melgarejo, M.; Rodriguez, C.: Nogueras, M.; Sánchez, A., An. Quím., 1983, 79C, 417-421.
9. The crystallographic data: Low. J.; Ferguson, G.; Cobo, J.; Melguizo, M., Nogueras, M., Sánchez, A. Acta Crystallogr. 1996, C52, 145.
10. H-1' values (for α-anomer this appears further downfield than that of the β-anomer) according to: Nishimura, T.; Shimizu, B., Chem. Pharm. Bull., 1965, 13, 803. Rayner, B.; Tapiero, C.; Imbach, J.L., in "Chemistry and Biology of Nucleosides and Nucleotides", Harmon, R.E.; Robins, R.K.; Townsend, L.B. eds, Academic Press, New York, 1978, p. 229.
11. H-1' values (for α-anomer this appears further downfield than that of the β-anomer) according to: Nishimura, T.; Shimizu, B., Chem. Pharm. Bull., 1965, 13, 803. Rayner, B.; Tapiero, C.; Imbach, J.L., in "Chemistry and Biology of Nucleosides and Nucleotides", Harmon, R.E.; Robins, R.K.; Townsend, L.B. eds, Academic Press, New York, 1978, p. 229.
12. Cook, P.D.; Rousseau, R.J.; Mian, A.M.; Dea, P.; Meyer Jr, R.B.; Robins, R.K., J. Am. Chem. Soc., 1976, 98, 1492.
13. Robins, M.J.; Maccoss, M., in "Chemistry and Biology of Nucleosides and Nucleotides", Harmon, R.E.; Robins, R.K.; Townsend, L.B. eds, Academic Press, New York, 1978, p. 311.
14. Nogueras, M.; Cobo, J.; Quijano, M.L.; Melguizo, M.; Sánchez, A.; Melgarejo, M., Nucleosides & Nucleotides, 1994, 13, 447-457.
15. De Clercq, E., In: "Minutes of the European Symposium on "In Vitro and Ex Vivo Tests Systems to Rationalize Drug Design and Delivery", Editons de Santé, Paris, France (Editors: D. Crommelin; P. Couvreur; D.Duchêne), pp 108-125 (1994).