Novel and efficient syntheses of 3′,5′-diamino derivatives of 2′,3′,5′-trideoxycytidine and 2′,3′,5′-trideoxyadenosine. Protonation behavior of 3′,5′-diaminonucleosides

Tetrahedron

Volumn 59, Issue 29, 2003, Pages 5449-5456

  Lavandera, Iván ^a   Fernández, Susana ^a   Ferrero, Miguel ^a   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

3 ,5 diaminonucleosides; Ionization constants; Protonation studies

Indexed keywords

2',3',5' TRIDEOXYADENOSINE; 2',3',5' TRIDEOXYCYTIDINE; ADENOSINE DERIVATIVE; AMINO ACID DERIVATIVE; AMINONUCLEOSIDE; CYTIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; IONIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; PRIORITY JOURNAL; PROTON TRANSPORT; SYNTHESIS;

EID: 0038383704     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00870-6     Document Type: Article

References (35)

1. (a) Robins R.K., Revankar G.R. De Clercq E., Walker R.T. Antiviral Drug Development. 1998;11 Plenum, New York, (b) Chu C.K., Baker D.C. Nucleosides and Nucleotides as Antitumor and Antiviral Agents. 1993;Plenum Press, New York, (c) MacCoss M., Robins M.J. Wilman D.E.V. Chemistry of Antitumor Agents. 1990;261 Blackie and Son, UK, (d) Robins R.K., Kini G.D. Wilman D.E.V. Chemistry of Antitumor Agents. 1990;299 Blackie and Son, UK, (e) Townsend L.B. Chemistry of Nucleosides and Nucleotides. 1988;Plenum, New York.
2. (a) Robins R.K., Revankar G.R. De Clercq E., Walker R.T. Antiviral Drug Development. 1998;11 Plenum, New York, (b) Chu C.K., Baker D.C. Nucleosides and Nucleotides as Antitumor and Antiviral Agents. 1993;Plenum Press, New York, (c) MacCoss M., Robins M.J. Wilman D.E.V. Chemistry of Antitumor Agents. 1990;261 Blackie and Son, UK, (d) Robins R.K., Kini G.D. Wilman D.E.V. Chemistry of Antitumor Agents. 1990;299 Blackie and Son, UK, (e) Townsend L.B. Chemistry of Nucleosides and Nucleotides. 1988;Plenum, New York.
3. (a) Robins R.K., Revankar G.R. De Clercq E., Walker R.T. Antiviral Drug Development. 1998;11 Plenum, New York, (b) Chu C.K., Baker D.C. Nucleosides and Nucleotides as Antitumor and Antiviral Agents. 1993;Plenum Press, New York, (c) MacCoss M., Robins M.J. Wilman D.E.V. Chemistry of Antitumor Agents. 1990;261 Blackie and Son, UK, (d) Robins R.K., Kini G.D. Wilman D.E.V. Chemistry of Antitumor Agents. 1990;299 Blackie and Son, UK, (e) Townsend L.B. Chemistry of Nucleosides and Nucleotides. 1988;Plenum, New York.
4. (a) Robins R.K., Revankar G.R. De Clercq E., Walker R.T. Antiviral Drug Development. 1998;11 Plenum, New York, (b) Chu C.K., Baker D.C. Nucleosides and Nucleotides as Antitumor and Antiviral Agents. 1993;Plenum Press, New York, (c) MacCoss M., Robins M.J. Wilman D.E.V. Chemistry of Antitumor Agents. 1990;261 Blackie and Son, UK, (d) Robins R.K., Kini G.D. Wilman D.E.V. Chemistry of Antitumor Agents. 1990;299 Blackie and Son, UK, (e) Townsend L.B. Chemistry of Nucleosides and Nucleotides. 1988;Plenum, New York.
5. (a) Ferrero M., Gotor V. Chem. Rev. 100:2000;4319-4347 (b) Kool E.T. Chem. Rev. 97:1997;1473-1487.
6. (a) Ferrero M., Gotor V. Chem. Rev. 100:2000;4319-4347 (b) Kool E.T. Chem. Rev. 97:1997;1473-1487.
7. (a) Vince R., Hua M. J. Med. Chem. 33:1990;17-21 (b) Ozaki S., Akiyama T., Ike Y., Mori H., Hoshi A. Chem. Pharm. Bull. 37:1990;3405-3417.
8. (a) Vince R., Hua M. J. Med. Chem. 33:1990;17-21 (b) Ozaki S., Akiyama T., Ike Y., Mori H., Hoshi A. Chem. Pharm. Bull. 37:1990;3405-3417.
9. (a) Singh I., Hecker W., Prasad A.K., Parmar V.S., Seitz O. Chem. Commun. 2002;500-501 (b) Singh S.K., Kumar R., Wengel. J. Org. Chem. 63:1998;10035-10039 (c) Uhlman E., Peyman A. Chem. Rev. 90:1990;543-584.
10. (a) Singh I., Hecker W., Prasad A.K., Parmar V.S., Seitz O. Chem. Commun. 2002;500-501 (b) Singh S.K., Kumar R., Wengel. J. Org. Chem. 63:1998;10035-10039 (c) Uhlman E., Peyman A. Chem. Rev. 90:1990;543-584.
11. (a) Singh I., Hecker W., Prasad A.K., Parmar V.S., Seitz O. Chem. Commun. 2002;500-501 (b) Singh S.K., Kumar R., Wengel. J. Org. Chem. 63:1998;10035-10039 (c) Uhlman E., Peyman A. Chem. Rev. 90:1990;543-584.
12. (a) Suhadolnik R.J. Nucleosides as Biological Probes. 1979;Wiley, New York, (b) Suhadolnik R.J. Nucleoside Antibiotics. 1970;Wiley, New York.
13. (a) Suhadolnik R.J. Nucleosides as Biological Probes. 1979;Wiley, New York, (b) Suhadolnik R.J. Nucleoside Antibiotics. 1970;Wiley, New York.
14. (a) Robins M.J., Zou R., Hansske F., Wnuk S.F. Can. J. Chem. 75:1997;762-767 (b) García-Alles L.F., Magdalena J., Gotor V. J. Org. Chem. 61:1996;6980-6986 (c) Robins M.J., Hawrelak S.D., Hernandez A.E., Wnuk S.F. Nucleos. Nucleot. 11:1992;821-834 (d) Samano M.C., Robins M.J. Tetrahedron Lett. 30:1989;2329-2332 (e) Herdewijn P., Balzarini J., Masanori B., Pauwels R., Van Aerschot A., Janssen G., De Clercq E. J. Med. Chem. 31:1988;2040-2048 (f) Mengel R., Wiedner H. Chem. Ber. 109:1976;433-443.
15. (a) Robins M.J., Zou R., Hansske F., Wnuk S.F. Can. J. Chem. 75:1997;762-767 (b) García-Alles L.F., Magdalena J., Gotor V. J. Org. Chem. 61:1996;6980-6986 (c) Robins M.J., Hawrelak S.D., Hernandez A.E., Wnuk S.F. Nucleos. Nucleot. 11:1992;821-834 (d) Samano M.C., Robins M.J. Tetrahedron Lett. 30:1989;2329-2332 (e) Herdewijn P., Balzarini J., Masanori B., Pauwels R., Van Aerschot A., Janssen G., De Clercq E. J. Med. Chem. 31:1988;2040-2048 (f) Mengel R., Wiedner H. Chem. Ber. 109:1976;433-443.
16. (a) Robins M.J., Zou R., Hansske F., Wnuk S.F. Can. J. Chem. 75:1997;762-767 (b) García-Alles L.F., Magdalena J., Gotor V. J. Org. Chem. 61:1996;6980-6986 (c) Robins M.J., Hawrelak S.D., Hernandez A.E., Wnuk S.F. Nucleos. Nucleot. 11:1992;821-834 (d) Samano M.C., Robins M.J. Tetrahedron Lett. 30:1989;2329-2332 (e) Herdewijn P., Balzarini J., Masanori B., Pauwels R., Van Aerschot A., Janssen G., De Clercq E. J. Med. Chem. 31:1988;2040-2048 (f) Mengel R., Wiedner H. Chem. Ber. 109:1976;433-443.
17. (a) Robins M.J., Zou R., Hansske F., Wnuk S.F. Can. J. Chem. 75:1997;762-767 (b) García-Alles L.F., Magdalena J., Gotor V. J. Org. Chem. 61:1996;6980-6986 (c) Robins M.J., Hawrelak S.D., Hernandez A.E., Wnuk S.F. Nucleos. Nucleot. 11:1992;821-834 (d) Samano M.C., Robins M.J. Tetrahedron Lett. 30:1989;2329-2332 (e) Herdewijn P., Balzarini J., Masanori B., Pauwels R., Van Aerschot A., Janssen G., De Clercq E. J. Med. Chem. 31:1988;2040-2048 (f) Mengel R., Wiedner H. Chem. Ber. 109:1976;433-443.
18. (a) Robins M.J., Zou R., Hansske F., Wnuk S.F. Can. J. Chem. 75:1997;762-767 (b) García-Alles L.F., Magdalena J., Gotor V. J. Org. Chem. 61:1996;6980-6986 (c) Robins M.J., Hawrelak S.D., Hernandez A.E., Wnuk S.F. Nucleos. Nucleot. 11:1992;821-834 (d) Samano M.C., Robins M.J. Tetrahedron Lett. 30:1989;2329-2332 (e) Herdewijn P., Balzarini J., Masanori B., Pauwels R., Van Aerschot A., Janssen G., De Clercq E. J. Med. Chem. 31:1988;2040-2048 (f) Mengel R., Wiedner H. Chem. Ber. 109:1976;433-443.
19. (a) Robins M.J., Zou R., Hansske F., Wnuk S.F. Can. J. Chem. 75:1997;762-767 (b) García-Alles L.F., Magdalena J., Gotor V. J. Org. Chem. 61:1996;6980-6986 (c) Robins M.J., Hawrelak S.D., Hernandez A.E., Wnuk S.F. Nucleos. Nucleot. 11:1992;821-834 (d) Samano M.C., Robins M.J. Tetrahedron Lett. 30:1989;2329-2332 (e) Herdewijn P., Balzarini J., Masanori B., Pauwels R., Van Aerschot A., Janssen G., De Clercq E. J. Med. Chem. 31:1988;2040-2048 (f) Mengel R., Wiedner H. Chem. Ber. 109:1976;433-443.
20. (a) Pannecouque C., Busson R., Balzarini J., Claes P., De Clercq E., Herdewijn P. Tetrahedron. 51:1995;5369-5380 (b) Pannecouque C., Van Poppel K., Balzarini J., Claes P., De Clercq E., Herdewijn P. Nucleos. Nucleot. 14:1995;541-544 (c) Herdewijn P., Balzarini J., Pauwels R., Janssen G., Van Aerschot A., De Clercq E. Nucleos. Nucleot. 8:1989;1231-1257 (d) Lin T., Zhou R.-X., Scanlon K.J., Brubaker W.F. Jr., Lee J.J.S., Woods K., Humphreys C., Prusoff W.H. J. Med. Chem. 29:1986;681-686 (e) Lin T.-S., Prusoff W.H. J. Med. Chem. 21:1978;109-112.
21. (a) Pannecouque C., Busson R., Balzarini J., Claes P., De Clercq E., Herdewijn P. Tetrahedron. 51:1995;5369-5380 (b) Pannecouque C., Van Poppel K., Balzarini J., Claes P., De Clercq E., Herdewijn P. Nucleos. Nucleot. 14:1995;541-544 (c) Herdewijn P., Balzarini J., Pauwels R., Janssen G., Van Aerschot A., De Clercq E. Nucleos. Nucleot. 8:1989;1231-1257 (d) Lin T., Zhou R.-X., Scanlon K.J., Brubaker W.F. Jr., Lee J.J.S., Woods K., Humphreys C., Prusoff W.H. J. Med. Chem. 29:1986;681-686 (e) Lin T.-S., Prusoff W.H. J. Med. Chem. 21:1978;109-112.
22. (a) Pannecouque C., Busson R., Balzarini J., Claes P., De Clercq E., Herdewijn P. Tetrahedron. 51:1995;5369-5380 (b) Pannecouque C., Van Poppel K., Balzarini J., Claes P., De Clercq E., Herdewijn P. Nucleos. Nucleot. 14:1995;541-544 (c) Herdewijn P., Balzarini J., Pauwels R., Janssen G., Van Aerschot A., De Clercq E. Nucleos. Nucleot. 8:1989;1231-1257 (d) Lin T., Zhou R.-X., Scanlon K.J., Brubaker W.F. Jr., Lee J.J.S., Woods K., Humphreys C., Prusoff W.H. J. Med. Chem. 29:1986;681-686 (e) Lin T.-S., Prusoff W.H. J. Med. Chem. 21:1978;109-112.
23. (a) Pannecouque C., Busson R., Balzarini J., Claes P., De Clercq E., Herdewijn P. Tetrahedron. 51:1995;5369-5380 (b) Pannecouque C., Van Poppel K., Balzarini J., Claes P., De Clercq E., Herdewijn P. Nucleos. Nucleot. 14:1995;541-544 (c) Herdewijn P., Balzarini J., Pauwels R., Janssen G., Van Aerschot A., De Clercq E. Nucleos. Nucleot. 8:1989;1231-1257 (d) Lin T., Zhou R.-X., Scanlon K.J., Brubaker W.F. Jr., Lee J.J.S., Woods K., Humphreys C., Prusoff W.H. J. Med. Chem. 29:1986;681-686 (e) Lin T.-S., Prusoff W.H. J. Med. Chem. 21:1978;109-112.
24. (a) Pannecouque C., Busson R., Balzarini J., Claes P., De Clercq E., Herdewijn P. Tetrahedron. 51:1995;5369-5380 (b) Pannecouque C., Van Poppel K., Balzarini J., Claes P., De Clercq E., Herdewijn P. Nucleos. Nucleot. 14:1995;541-544 (c) Herdewijn P., Balzarini J., Pauwels R., Janssen G., Van Aerschot A., De Clercq E. Nucleos. Nucleot. 8:1989;1231-1257 (d) Lin T., Zhou R.-X., Scanlon K.J., Brubaker W.F. Jr., Lee J.J.S., Woods K., Humphreys C., Prusoff W.H. J. Med. Chem. 29:1986;681-686 (e) Lin T.-S., Prusoff W.H. J. Med. Chem. 21:1978;109-112.
25. Lavandera I., Fernández S., Ferrero M., Gotor V. J. Org. Chem. 66:2001;4079-4082.
26. Divakar K.J., Reese C.B. J. Chem. Soc., Perkin Trans. 1. 1982;1171-1176.
27. (a) Garrett E.R., Mehta P.J. J. Am. Chem. Soc. 94:1972;8532-8541 (b) Zoltewicz J.A., Clarck D.F. J. Org. Chem. 37:1972;1193-1197 (c) Romero R., Stein R., Cordes H.G., Cordes E.H. J. Am. Chem. Soc. 100:1978;7620-7624.
28. (a) Garrett E.R., Mehta P.J. J. Am. Chem. Soc. 94:1972;8532-8541 (b) Zoltewicz J.A., Clarck D.F. J. Org. Chem. 37:1972;1193-1197 (c) Romero R., Stein R., Cordes H.G., Cordes E.H. J. Am. Chem. Soc. 100:1978;7620-7624.
29. (a) Garrett E.R., Mehta P.J. J. Am. Chem. Soc. 94:1972;8532-8541 (b) Zoltewicz J.A., Clarck D.F. J. Org. Chem. 37:1972;1193-1197 (c) Romero R., Stein R., Cordes H.G., Cordes E.H. J. Am. Chem. Soc. 100:1978;7620-7624.
30. Gunter H. NMR Spectroscopy: Basic Principles Concepts and Applications in Chemistry. 2nd ed. 1995;Wiley, New York.
31. Gans P., Sabatini A., Vacca A. J. Chem. Soc., Dalton Trans. 1985;1195-1200.
32. Fontes N., Partridge J., Halling P.J., Barreiros S. Biotechnol. Bioeng. 77:2002;296-305.
33. Structure of compound 7 is labelled as follows:
34. Chen J.-K., Schultz R.G., Lloyd D.H., Gryanov S.M. Nucleic Acids Res. 23:1995;2661-2668.
35. Linkletter B.A., Szabo I.E., Bruice T.C. Nucleic Acids Res. 29:2001;2370-2376.