Synthesis of enterolactone and enterodiol precursors as potential inhibitors of human estrogen synthetase (aromatase)

Steroids. 2000 Aug;65(8):437-41. doi: 10.1016/s0039-128x(00)00104-5.

Abstract

A series of variably substituted derivatives of lignan lactones and diols were prepared using tandem conjugate addition reaction as a key step. These theoretical precursors of the mammalian lignans enterolactone 1 and enterodiol 3 are moderate or weak inhibitors of human aromatase activity.

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemical synthesis
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / pharmacology
  • Aromatase Inhibitors*
  • Catechols / chemical synthesis*
  • Catechols / pharmacology*
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Lignans / chemistry
  • Phenols / chemical synthesis*
  • Phenols / pharmacology*

Substances

  • 3'-demethoxysecoisolariciresinol
  • 3-demethoxy-3'-O-demethylmatairesinol
  • Aromatase Inhibitors
  • Catechols
  • Enzyme Inhibitors
  • Lignans
  • Phenols
  • 2,3-bis(3'-hydroxybenzyl)butane-1,4-diol
  • 4-Butyrolactone
  • 2,3-bis(3'-hydroxybenzyl)butyrolactone