Synthesis and conformational analysis of pyrimidine nucleoside analogues with a rigid sugar moiety

Bioorg Med Chem. 1995 Apr;3(4):397-402. doi: 10.1016/0968-0896(95)00028-f.

Abstract

In order to obtain rigidity within the sugar moiety of nucleosides, some bicyclic pyrimidine nucleoside analogues were synthesized starting from cyclopentanone. The C-3' is fused to C-4' via a propylene linker in order to obtain a [3.3.0]-bicyclic ring system wherein the sugar moiety should be restricted to mainly the C-1'-exo conformation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry*
  • Antiviral Agents / pharmacology
  • Chromatography
  • Cyclopentanes / chemistry*
  • Cytidine / chemistry
  • HIV-1 / drug effects
  • HIV-1 / enzymology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Pyrimidines / chemistry*
  • Reverse Transcriptase Inhibitors / pharmacology
  • Software
  • Structure-Activity Relationship

Substances

  • Antiviral Agents
  • Cyclopentanes
  • Pyrimidines
  • Reverse Transcriptase Inhibitors
  • Cytidine
  • pyrimidine