Synthesis and highly potent hypolipidemic activity of alpha-asarone- and fibrate-based 2-acyl and 2-alkyl phenols as HMG-CoA reductase inhibitors

Bioorg Med Chem. 2014 Nov 1;22(21):5871-82. doi: 10.1016/j.bmc.2014.09.022. Epub 2014 Sep 19.

Abstract

In the search for new potential hypolipidemic agents, the present study focused on the synthesis of 2-acyl phenols (6a-c and 7a-c) and their saturated side-chain alkyl phenols (4a-c and 5a-c), and on the evaluation of their hypolipidemic activity using a murine Tyloxapol-induced hyperlipidemic protocol. The whole series of compounds 4-7 greatly and significantly reduced elevated serum levels of total cholesterol, LDL-cholesterol, and triglycerides, with series 6 and 7 showing the greatest potency ever found in our laboratory. At the minimum dose (25mg/kg/day), the latter compounds lowered cholesterol by 68-81%, LDL by 72-86%, and triglycerides by 59-80%. This represents a comparable performance than that shown by simvastatin. Experimental evidence and docking studies suggest that the activity of these derivatives is associated with the inhibition of HMG-CoA reductase.

Keywords: 2-Acyl phenols; 2-Alkyl phenols; Docking; HMG-CoA reductase; Hypolipidemic; Phenoxyacetic.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allylbenzene Derivatives
  • Animals
  • Anisoles / chemistry*
  • Anisoles / pharmacology*
  • Binding Sites
  • Catalytic Domain
  • Cholesterol / blood
  • Cholesterol, LDL / blood
  • Crystallography, X-Ray
  • Enzyme Activation / drug effects
  • Humans
  • Hydroxymethylglutaryl CoA Reductases / chemistry
  • Hydroxymethylglutaryl CoA Reductases / metabolism
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors / chemical synthesis*
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors / metabolism
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors / pharmacology*
  • Male
  • Mice
  • Mice, Inbred ICR
  • Molecular Conformation
  • Molecular Docking Simulation
  • Phenols / chemistry*
  • Phenols / pharmacology*
  • Protein Binding
  • Triglycerides / blood
  • Weight Gain / drug effects

Substances

  • Allylbenzene Derivatives
  • Anisoles
  • Cholesterol, LDL
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors
  • Phenols
  • Triglycerides
  • asarone
  • Cholesterol
  • Hydroxymethylglutaryl CoA Reductases