Synthesis of Novel Nucleoside Analogues Built on a Bicyclo[4.1.0]heptane Scaffold

J Org Chem. 2015 Oct 2;80(19):9495-505. doi: 10.1021/acs.joc.5b01413.

Abstract

A new class of carbocyclic nucleoside analogues built on a bicyclo[4.1.0]heptane scaffold, a perspective novel pseudosugar pattern, have been conceived as anti-HSV agents on the basis of initial protein-ligand docking studies. The asymmetric synthesis of a series of these compounds incorporating different nucleobases has been efficiently completed starting from 1,4-cyclohexanedione.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / chemistry
  • Crystallography, X-Ray
  • Cyclohexanones / chemistry*
  • Heptanes / chemical synthesis*
  • Heptanes / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Stereoisomerism

Substances

  • 1,4-cyclohexanedione
  • Bridged Bicyclo Compounds
  • Cyclohexanones
  • Heptanes
  • Nucleosides