Synthesis and screening of aromatase inhibitory activity of substituted C19 steroidal 17-oxime analogs

Molecules. 2011 Nov 28;16(12):9868-85. doi: 10.3390/molecules16129868.

Abstract

The synthesis and aromatase inhibitory activity of androst-4-en-, androst-5-en-, 1β,2β-epoxy- and/or androsta-4,6-dien-, 4β,5β-epoxyandrostane-, and 4-substituted androst-4-en-17-oxime derivatives are described. Inhibition activity of synthesized compounds was assessed using aromatase enzyme and [1β-3H]androstenedione as substrate. Most of the compounds displayed similar to or more aromatase inhibitory activity than formestane (74.2%). 4-Chloro-3β-hydroxy-4-androsten-17-one oxime (14, 93.8%) showed the highest activity, while 4-azido-3β-hydroxy-4-androsten-17-one oxime (17, 32.8%) showed the lowest inhibitory activity for aromatase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aromatase / metabolism
  • Aromatase Inhibitors / analysis*
  • Aromatase Inhibitors / chemical synthesis*
  • Aromatase Inhibitors / chemistry
  • Aromatase Inhibitors / pharmacology
  • Drug Evaluation, Preclinical
  • Humans
  • Magnetic Resonance Spectroscopy
  • Oximes / analysis*
  • Oximes / chemical synthesis*
  • Oximes / chemistry
  • Oximes / pharmacology
  • Steroids / chemistry*
  • Steroids / metabolism*

Substances

  • Aromatase Inhibitors
  • Oximes
  • Steroids
  • Aromatase