Synthesis of a tetrasubstituted bicyclo [2.2.2] octane as a potential inhibitor of influenza virus sialidase

Bioorg Med Chem Lett. 1999 Feb 22;9(4):611-4. doi: 10.1016/s0960-894x(99)00033-5.

Abstract

A novel synthesis of the bicyclo [2.2.2] octane ring system has been achieved utilising a tandem Henry cyclisation as the key stage. This chemistry has been employed in the synthesis of a potential inhibitor of influenza virus sialidase.

MeSH terms

  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / chemistry
  • Bridged Bicyclo Compounds / pharmacology
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / pharmacology
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Influenza A virus / enzymology*
  • Influenza B virus / enzymology*
  • Neuraminidase / antagonists & inhibitors*

Substances

  • 4-acetylamino-3-hydroxy-5-n-propoxybicyclo(2.2.2)octane-1-carboxylic acid
  • Bridged Bicyclo Compounds
  • Carboxylic Acids
  • Enzyme Inhibitors
  • Neuraminidase