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

Devos, E.;Esmans, EL.;Lepoivre, JA.;Alderweireldt, FC.;De Clercq, Etienne;et.al.
(1991) Nucleosides and Nucleotides — Vol. 10, n° 7, p. 1573-1598 (1991)

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  • Devos, E.University of Antwerp (RUCA), Laboratory for Organic Chemistry
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  • Esmans, EL.University of Antwerp (RUCA), Laboratory for Organic Chemistry
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  • Lepoivre, JA.University of Antwerp (RUCA), Laboratory for Organic Chemistry
    Author
  • Alderweireldt, FC.University of Antwerp (RUCA), Laboratory for Organic Chemistry
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  • François, PierreUCLouvain
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  • Touillaux, RolandUCLouvain
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  • De Clercq, EtienneUCLouvain
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Abstract
2-(2-Deoxy-D-erythro-pent-1-enofuranosyl)pyridine and its methyl analogues have been prepared by treatment of the corresponding 2',3'-O-isopropylidene-D-ribofuranosyl derivatives with several bases such as sodium amide, tert.BuOK, EtONa, lithium tetramethylpiperidide (LTMP) and phenyl lithium (PhLi). PhLi and tert.BuOK gave the best results. The products thus obtained showed cytostatic activity against human tumor cell lines, in particular MT-4, a human T-lymphocyte cell line. No antiviral activity was noted at subtoxic concentrations.
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Devos, E., Esmans, EL., Lepoivre, JA., Alderweireldt, FC., Dommisse, RA., François, P., Touillaux, R., Balzarini, J., & De Clercq, E. (1991). Synthesis and Biological Evaluation of 2-(2-deoxy-d-erythro-pent-1-enofuranosyl)pyridine C-nucleosides. Nucleosides and Nucleotides, 10(7), 1573-1598. https://doi.org/10.1080/07328319108046683 (Original work published 1991)