Synthesis and anabolic/androgenic evaluation of novel 9alpha-fluorosteroids

Eur J Med Chem. 2009 Nov;44(11):4567-71. doi: 10.1016/j.ejmech.2009.06.025. Epub 2009 Jul 1.

Abstract

3Beta,11beta-dihydroxy-9alpha-fluor-5alpha-androstane-17-one (2), 3beta-acetoxy-9alpha-fluor-11beta-hydroxy-5alpha-androstane-17-one (3), 3beta-acetoxy-9alpha-fluor-11beta,17beta-dihydroxy-5alpha-androstane (4), 3beta,17beta-diacetoxy-9alpha-fluor-11beta-hydroxy-5alpha-androstane (5), 3beta-acetoxy-9alpha-fluor-11beta-hydroxy-5alpha-androstane 17beta-propionate (6), 3beta-acetoxy-9alpha-fluor-11beta-hydroxy-5alpha-androstane 17beta-enanthate (7), 3beta-acetoxy-9alpha-fluor-11beta-hydroxy-5alpha-androstane 17beta-isobutyrate (8) were synthesized in the present study. Compounds 2 and 8 exhibited higher anabolic activity than the rest of the synthesized compounds. The structure of all these newly synthesized compounds was confirmed by analytic spectral data (mass, (1)H NMR and (13)C NMR).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anabolic Agents / chemical synthesis
  • Anabolic Agents / chemistry*
  • Anabolic Agents / pharmacology*
  • Androgens / chemical synthesis
  • Androgens / chemistry*
  • Androgens / pharmacology*
  • Androstanes / chemical synthesis
  • Androstanes / chemistry*
  • Androstanes / pharmacology*
  • Animals
  • Fluorine / chemistry
  • Fluorine / pharmacology
  • Male
  • Muscles / drug effects
  • Organ Size / drug effects
  • Prostate / drug effects
  • Rats
  • Rats, Wistar
  • Seminal Vesicles / drug effects

Substances

  • Anabolic Agents
  • Androgens
  • Androstanes
  • Fluorine