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Synthesis and Biological Evaluation of 2-(2-deoxy-d-erythro-pent-1-enofuranosyl)pyridine C-nucleosides

Bibliographic reference Devos, E. ; Esmans, EL. ; Lepoivre, JA. ; Alderweireldt, FC. ; Dommisse, RA. ; et. al. Synthesis and Biological Evaluation of 2-(2-deoxy-d-erythro-pent-1-enofuranosyl)pyridine C-nucleosides. In: Nucleosides and Nucleotides, Vol. 10, no. 7, p. 1573-1598 (1991)
Permanent URL http://hdl.handle.net/2078.1/50874
  1. Mitsuya H., Broder S., Inhibition of the in vitro infectivity and cytopathic effect of human T-lymphotrophic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV) by 2',3'-dideoxynucleosides., 10.1073/pnas.83.6.1911
  2. Balzarini Jan, Pauwels Rudi, Herdewijn Piet, De Clercq Erik, Cooney David A., Kang Gil-Jong, Dalal Maha, Johns David G., Broder Samuel, Potent and selective anti-HTLV-IIILAV activity of 2′,3′-dideoxycytidinene, the 2′,3′-unsaturated derivative of 2′,3′-dideoxycytidine, 10.1016/0006-291x(86)90793-x
  3. Baba Masanori, Pauwels Rudi, Herdewijn Piet, De Clercq Erik, Desmyter Jan, Vandeputte Michel, Both 2′,3′-dideoxythymidine and its 2′,3′-unsaturated derivative (2′,3′-dideoxythymidinene) are potent and selective inhibitors of human immunodeficiency virus replication in vitro, 10.1016/0006-291x(87)90460-8
  4. Balzarini J., Mol. Pharmacol., 32, 162 (1987)
  5. Chu C. K., Bhadti V. S., Doboszewski B., Gu Z. P., Kosugi Y., Pullaiah K. C., Van Roey P., General syntheses of 2',3'-dideoxynucleosides and 2',3'-didehydro-2',3'-dideoxynucleosides, 10.1021/jo00270a036
  6. Robins Morris J., Jones Roger A., Nucleic acid related compounds. 9. Synthesis of 6-amino-9-(2-deoxy-D-erythro-pent-1-enofuranosyl)purine, the first 1', 2'-unsaturated purine nucleoside, 10.1021/jo00915a031
  7. Robins Morris J., Trip E.M., Nucleic acid related compounds. 13, 10.1016/s0040-4039(01)91909-4
  8. Robins Morris J., Jones Roger A., Mengel Rudolf, Nucleic acid related compounds. 23. Transformation of ribonucleoside 2',3'-O-ortho esters into unsaturated and deoxy sugar nucleosides via enol ester-substituted iodo intermediates, 10.1021/ja00441a054
  9. Hennen William J., Robins Roland K., Synthesis of 5-(β-D-ribofuranosyl)-1,2,4-oxadiazole-3-carboxamide, 10.1002/jhet.5570220656
  10. Maeba Isamu, Kitaori Kazuhiro, Ito Chihiro, C-nucleosides. 10. Synthesis of 1,3-dimethyl-7-(.beta.-D-ribofuranosyl)lumazine, 10.1021/jo00277a033
  11. Allard Patrice, Tam Huynh Dinh, Gouyette Catherine, Igolen Jean, Chermann Jean-Claude, Barre-Sinoussi Francoise, 2-L-Rhamnopyranosyl[1,2,4]triazolo[1,5-a]pyridine. 4' and 3' Oxidation products. Synthesis and structure-activity relationships, 10.1021/jm00143a006
  12. Esmans E. L., Belmans M., Vryens I., Dommisse R., Lepoivre J. A., Alderweireldt F. C., Approach to the Synthesis of 2-(D-Ribofuranosyl)-Pyridine Compounds, 10.1080/07328318508077859
  13. Belmans M., Vrijens I., Esmans E., Dommisse R., Lepoivre J., Alderweireldt F., Townsend L., Wotring L., Balzarini J., Clercq E. De, Synthests and Biological Evaluation of a Series of Substituted-2-Pyridine-C-Nucleosides. Part II, 10.1080/07328318608068685
  14. Belmans M., Vrijens I., Esmans E. L., Dommisse R. A., Lepoivre J. A., Alderweireldt F. C., Townsend L. B., Wotring L. L., Balzarini J., Clercq E. De, Synthesis and Biological Evaluation of a Series of Substituted Pyridine-C-Nucleosides. Part V: 3-Chloro-4-(D-Ribofuranosyl)Pyridine and 3-(D-Ribofuranosyl)-2-Pyridone, 10.1080/07328318908054176
  15. Alderweireldt F. C., Vrijens I., Esmans E. L., Wotring L. L., Townsend L. B., Balzarini J., De Clercq E., Synthesis and Biological Evaluation of 2-Carbamoyl-5-D-Ribofuranosylpyridine, 10.1080/07328318908054238
  16. Joos P., Nucleosides & Nucleotides
  17. Kabat Marek M., Pankiewicz Krzysztof W., Watanabe Kyoichi A., Nucleosides. 141. Synthesis of 5-.beta.-D-ribofuranosylnicotinamide and its N-methyl derivative. The isosteric and isoelectronic analogs of nicotinamide nucleoside, 10.1021/jm00388a030
  18. Pankiewicz Krzysztof W., Sochacka Elzbieta, Kabat Marek M., Ciszewski Lech A., Watanabe Kyoichi A., Nucleosides. 151. Efficient synthesis of 5-(.beta.-D-ribofuranosyl)nicotinamide and its .alpha.-isomer, 10.1021/jo00250a013
  19. Kabat M. M., Chem. Pharm. Bull., 36, 634 (1988)
  20. Tam Steve Y. K., Klein Robert S., De las Heras Frederico G., Fox Jack J., Nucleosides. 113. Synthesis of 6-(.beta.-D-ribofuranosyl)pyrimidines. A new class of pyrimidine C-nucleosides, 10.1021/jo00394a024
  21. Marsais F., J. Chem. Res. (S) (1982)
  22. Chu C. K., El-kabbani F. M., Thompson B. B., Determination of the Anomeric Configuration of C-Nucleosides by1H and13C NMR Spectroscopy, 10.1080/07328318408079416
  23. Fourrey Jean Louis, Jouin Patrick, S-Nucleoside photorearrangement. Access to pyridine pseudonucleosides, 10.1021/jo01325a039
  24. Pompon A., Nucleot. & Biol. Appl., 303 (1982)
  25. Vrijens I., Bio-Organic Heterocycles, 207 (1986)
  26. Francois P., Sonveaur E., Touillaux R., A High Field NMR Study of 2′-Deoxyribo-C-Nucleosides, 10.1080/07328319008045152
  27. Haasnoot C. A. G., de Leeuw F. A. A. M., de Leeuw H. P. M., Altona C., The relationship between proton-proton NMR coupling constants and substituent electronegativities. II—conformational analysis of the sugar ring in nucleosides and nucleotides in solution using a generalized Karplus equation, 10.1002/mrc.1270150111
  28. Rosemeyer H., Tóth G., Seela F., Assignment of Anomeric Configuration of D-Ribo-, Arabino-, 2′-Deoxyribo-, and 2′,3′-Dideoxyribonucleosides by Noe Difference Spectroscopy, 10.1080/07328318908054200
  29. De Clercq E., Mol. Pharmacol., 19, 321 (1981)
  30. De Clercq E., Descamps J., Verhelst G., Walker R. T., Jones A. S., Torrence P. F., Shugar D., Comparative Efficacy of Antiherpes Drugs against Different Strains of Herpes Simplex Virus, 10.1093/infdis/141.5.563
  31. De Clercq E, Antiviral and antimetabolic activities of neplanocins., 10.1128/aac.28.1.84
  32. Balzarini J., Molec. Pharmacol., 33, 243 (1988)