Synthesis and biological activity of new HMG-CoA reductase inhibitors. 1. Lactones of pyridine- and pyrimidine-substituted 3,5-dihydroxy-6-heptenoic (-heptanoic) acids

J Med Chem. 1990 Jan;33(1):52-60. doi: 10.1021/jm00163a010.

Abstract

Lactones of pyridine- and pyrimidine-substituted 3,5-dihydroxy-6-heptenoic (-heptanoic) acids 2-4 have been synthesized. Extensive exploration of structure-activity relationships led to several compounds exceeding the inhibitory activity of mevinolin (1b) on HMG-CoA reductase, both in vitro and in vivo. First clinical trials with 2i (HR 780) are in preparation.

MeSH terms

  • Acetates / metabolism
  • Animals
  • Anticholesteremic Agents
  • Chemical Phenomena
  • Chemistry
  • Cholesterol / biosynthesis
  • Cholesterol / blood
  • Heptanoic Acids / chemical synthesis
  • Heptanoic Acids / pharmacology*
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors*
  • Lactones / chemical synthesis
  • Lactones / pharmacology*
  • Liver / enzymology
  • Liver Neoplasms, Experimental / metabolism
  • Male
  • Molecular Conformation
  • Molecular Structure
  • Pyridines / chemical synthesis
  • Pyridines / pharmacology*
  • Pyrimidines / chemical synthesis
  • Pyrimidines / pharmacology*
  • Rabbits
  • Rats
  • Structure-Activity Relationship
  • Tumor Cells, Cultured
  • X-Ray Diffraction

Substances

  • Acetates
  • Anticholesteremic Agents
  • Heptanoic Acids
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors
  • Lactones
  • Pyridines
  • Pyrimidines
  • HR 780
  • Cholesterol