4'-AZA-3',5'-dihomothymidine and derivatives

J. M J Tronchet, M. Iznaden, F. Barbalat-Rey, I. Komáromi, N. Dolatshahi, G. Bernardinelli

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

A series of 3'-branched 4'-azanucleoside analogues have been prepared. These compounds comprise three asymmetric atoms, two carbons and one nitrogen. They constitute nucleoside analogues imparted with a 'flickering configuration', the nitrogen inversion replacing a D-L epimerization of their natural congeners. The 1',3'-cis and 1',3'-trans isomers have been separated and their configuration established by 1H NMR and the X-ray diffraction structure of one crystalline example. The configurations of the frozen invertomers were assessed by low temperature 1H NMR experiments assisted by molecular mechanics simulations. None of these compounds exhibited any significant in vitro antiviral activity.

Original languageEnglish
Pages (from-to)1737-1758
Number of pages22
JournalNucleosides and Nucleotides
Volume14
Issue number8
Publication statusPublished - 1995

Fingerprint

Nitrogen
Nuclear magnetic resonance
Flickering
Derivatives
Molecular mechanics
Mechanics
Nucleosides
X-Ray Diffraction
Isomers
Antiviral Agents
Carbon
Crystalline materials
X ray diffraction
Atoms
Temperature
Experiments
Proton Magnetic Resonance Spectroscopy
In Vitro Techniques

ASJC Scopus subject areas

  • Biochemistry
  • Genetics

Cite this

Tronchet, J. M. J., Iznaden, M., Barbalat-Rey, F., Komáromi, I., Dolatshahi, N., & Bernardinelli, G. (1995). 4'-AZA-3',5'-dihomothymidine and derivatives. Nucleosides and Nucleotides, 14(8), 1737-1758.

4'-AZA-3',5'-dihomothymidine and derivatives. / Tronchet, J. M J; Iznaden, M.; Barbalat-Rey, F.; Komáromi, I.; Dolatshahi, N.; Bernardinelli, G.

In: Nucleosides and Nucleotides, Vol. 14, No. 8, 1995, p. 1737-1758.

Research output: Contribution to journalArticle

Tronchet, JMJ, Iznaden, M, Barbalat-Rey, F, Komáromi, I, Dolatshahi, N & Bernardinelli, G 1995, '4'-AZA-3',5'-dihomothymidine and derivatives', Nucleosides and Nucleotides, vol. 14, no. 8, pp. 1737-1758.
Tronchet JMJ, Iznaden M, Barbalat-Rey F, Komáromi I, Dolatshahi N, Bernardinelli G. 4'-AZA-3',5'-dihomothymidine and derivatives. Nucleosides and Nucleotides. 1995;14(8):1737-1758.
Tronchet, J. M J ; Iznaden, M. ; Barbalat-Rey, F. ; Komáromi, I. ; Dolatshahi, N. ; Bernardinelli, G. / 4'-AZA-3',5'-dihomothymidine and derivatives. In: Nucleosides and Nucleotides. 1995 ; Vol. 14, No. 8. pp. 1737-1758.
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