New aromatase inhibitors. Synthesis and inhibitory activity of pyridinyl-substituted flavanone derivatives

Bioorg Med Chem Lett. 2002 Apr 8;12(7):1059-61. doi: 10.1016/s0960-894x(02)00072-0.

Abstract

Two (E)-pyridinyl-substituted flavanone derivatives were synthesized and UV irradiation of these compounds afforded a Z-enriched mixture. These products were tested for their ability to inhibit the cytochrome P450 aromatase. It was observed that the introduction of a pyridinylmethylene group at carbon 3 on flavanone nucleus led to a significant increase of aromatase inhibitory effect. Moreover, configuration had a substantial influence on the aromatase inhibitory activity since (E)-isomers were found to be more active than (Z)-isomers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Androstenedione / chemistry
  • Androstenedione / metabolism
  • Aromatase Inhibitors*
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Flavanones*
  • Flavonoids / chemical synthesis*
  • Flavonoids / chemistry*
  • Flavonoids / pharmacology
  • Humans
  • In Vitro Techniques
  • Male
  • Microsomes / drug effects
  • Microsomes / enzymology
  • Models, Molecular
  • Placenta / metabolism
  • Pyridines / chemistry*
  • Structure-Activity Relationship

Substances

  • Aromatase Inhibitors
  • Enzyme Inhibitors
  • Flavanones
  • Flavonoids
  • Pyridines
  • Androstenedione
  • pyridine
  • flavanone