3-Hydroxy-3-methylglutaryl-coenzyme A reductase inhibitors. 8. Side chain ether analogues of lovastatin

J Med Chem. 1991 Aug;34(8):2474-7. doi: 10.1021/jm00112a024.


A general route for preparing side chain ether analogues of lovastatin is presented. These analogues proved to be weaker inhibitors of HMG-CoA reductase than the corresponding side chain ester analogues. Interestingly, inhibitory potency was enhanced markedly when the 4-fluoro group was incorporated in the aromatic moiety of the side chain benzyl group of 2d.

Publication types

  • Comparative Study

MeSH terms

  • Chemical Phenomena
  • Chemistry
  • Esters
  • Ethers
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors*
  • Lovastatin / analogs & derivatives*
  • Lovastatin / chemical synthesis
  • Lovastatin / pharmacology
  • Molecular Structure
  • Structure-Activity Relationship


  • Esters
  • Ethers
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors
  • 6-(2-(8-((4-fluorobenzyl)oxy)-1,2,6,7,8,8a-hexahydro-2,6-dimethyl-1-naphthyl)ethyl)-4-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one
  • Lovastatin