Preparation of 20-(hydroxymethyl)-4-methyl-4-aza-2-oxa-5 alpha-pregnan-3-one as an inhibitor of testosterone 5 alpha-reductase

J Med Chem. 1985 Jun;28(6):831-3. doi: 10.1021/jm00383a026.

Abstract

20-(Hydroxymethyl)-4-methyl-4-aza-2-oxa-5 alpha-pregnan-3-one and the corresponding 3-thione were synthesized with use of 20-(hydroxymethyl)-4-methyl-4-aza-5 alpha-pregnan-3-one as the starting material. The compounds were tested in vitro for inhibition of testosterone 5 alpha-reductase and found to be weak inhibitors with Ki's in the 10(-7) range.

MeSH terms

  • 5-alpha Reductase Inhibitors*
  • Animals
  • Enzyme Inhibitors / chemical synthesis
  • In Vitro Techniques
  • Kinetics
  • Male
  • Oxidoreductases / antagonists & inhibitors*
  • Pregnanes / chemical synthesis*
  • Pregnanes / pharmacology
  • Prostate / enzymology
  • Rats
  • Steroids, Heterocyclic / chemical synthesis*
  • Steroids, Heterocyclic / pharmacology

Substances

  • 5-alpha Reductase Inhibitors
  • Enzyme Inhibitors
  • Pregnanes
  • Steroids, Heterocyclic
  • 20-(hydroxymethyl)-4-methyl-4-aza-2-oxapregnan-3-one
  • Oxidoreductases