Anti-HIV derivatives of 1-(2,3-dideoxy-3-n-hydroxyamino-β-d-thre o-pentofu ranosyl) thymine

Jean M T Tronchet, Martina Zsely, Karel Capek, I. Komáromi, Michel Geoffroy, Erik De Clercq, Jan Balzarini

Research output: Contribution to journalArticle

19 Citations (Scopus)

Abstract

Representative examples of the title compounds including bicyclic analogs (7–9) in which a perhydro-l,3-oxazine is ortho-iused to the furanose ring, have been prepared in good to excellent yields. Compounds 5 and 7 showed marked activity against HTV-1 and HTV-2 replication in CEM cells (50% inhibitory concentration: 0.80-4.3(ig/mL). Their di-O-acetylated (6) and mono-O-acetylated (8) derivatives were considerably less effective. To the best of our knowledge, these fi-D-threo anti-HIV nucleoside analogs constitute the first examples of anti-HTV active nucleosides bearing this configuration.

Original languageEnglish
Pages (from-to)1871-1889
Number of pages19
JournalNucleosides and Nucleotides
Volume13
Issue number9
DOIs
Publication statusPublished - Sep 1 1994

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Thymine
Nucleosides
HIV-1
Bearings (structural)
Oxazines
Derivatives
Inhibitory Concentration 50
HIV
RHO(D) antibody

ASJC Scopus subject areas

  • Biochemistry
  • Genetics

Cite this

Tronchet, J. M. T., Zsely, M., Capek, K., Komáromi, I., Geoffroy, M., Clercq, E. D., & Balzarini, J. (1994). Anti-HIV derivatives of 1-(2,3-dideoxy-3-n-hydroxyamino-β-d-thre o-pentofu ranosyl) thymine. Nucleosides and Nucleotides, 13(9), 1871-1889. https://doi.org/10.1080/15257779408010670

Anti-HIV derivatives of 1-(2,3-dideoxy-3-n-hydroxyamino-β-d-thre o-pentofu ranosyl) thymine. / Tronchet, Jean M T; Zsely, Martina; Capek, Karel; Komáromi, I.; Geoffroy, Michel; Clercq, Erik De; Balzarini, Jan.

In: Nucleosides and Nucleotides, Vol. 13, No. 9, 01.09.1994, p. 1871-1889.

Research output: Contribution to journalArticle

Tronchet, JMT, Zsely, M, Capek, K, Komáromi, I, Geoffroy, M, Clercq, ED & Balzarini, J 1994, 'Anti-HIV derivatives of 1-(2,3-dideoxy-3-n-hydroxyamino-β-d-thre o-pentofu ranosyl) thymine', Nucleosides and Nucleotides, vol. 13, no. 9, pp. 1871-1889. https://doi.org/10.1080/15257779408010670
Tronchet, Jean M T ; Zsely, Martina ; Capek, Karel ; Komáromi, I. ; Geoffroy, Michel ; Clercq, Erik De ; Balzarini, Jan. / Anti-HIV derivatives of 1-(2,3-dideoxy-3-n-hydroxyamino-β-d-thre o-pentofu ranosyl) thymine. In: Nucleosides and Nucleotides. 1994 ; Vol. 13, No. 9. pp. 1871-1889.
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