Lipid-lowering (hetero)aromatic tetrahydro-1,4-oxazine derivatives with antioxidant and squalene synthase inhibitory activity

J Med Chem. 2008 Sep 25;51(18):5861-5. doi: 10.1021/jm800663w.

Abstract

A number of newly synthesized 2-[4-(hetero)aromatic]phenyl-2-hydroxy-tetrahydro-1,4-oxazine derivatives were found to inhibit lipid peroxidation (IC50 of the most potent was 20 microM) as well as rat squalene synthase (IC50 for most between 1-10 microM). Antidyslipidemic action was demonstrated in vivo: the most active compound decreased triglycerides, total cholesterol, and LDL-cholesterol of hyperlipidemic rats by 64, 67, and 82%, respectively, at 56 micromol/kg (ip). Most of the novel compounds are more active than the structurally related and reference biphenyl-morpholine, pointing to useful structural approaches for the design of antiatherosclerotic agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Cholesterol / blood
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Farnesyl-Diphosphate Farnesyltransferase / antagonists & inhibitors*
  • Hypolipidemic Agents / chemistry
  • Hypolipidemic Agents / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Microsomes, Liver / drug effects
  • Microsomes, Liver / enzymology
  • Morpholines / chemistry
  • Morpholines / pharmacology*
  • Rats
  • Triglycerides / blood

Substances

  • Antioxidants
  • Enzyme Inhibitors
  • Hypolipidemic Agents
  • Morpholines
  • Triglycerides
  • Cholesterol
  • Farnesyl-Diphosphate Farnesyltransferase