Aldosterone antagonists. 4. Synthesis and activities of steroidal 6,6-ethylene-15,16-methylene 17-spirolactones

J Med Chem. 1991 Aug;34(8):2464-8. doi: 10.1021/jm00112a022.

Abstract

Several steroidal 6,6-ethylene-15,16-methylene 17-spirolactones were synthesized to find new progestogens that exhibit both progestational and antimineralocorticoidal activities. The influence of substituents in the 10- and 13-position of the steroidal framework on both properties was investigated. It was found that only compound 12, carrying methyl groups at the 10- and 13-positions, possesses high progestational and antimineralocorticoidal activity.

Publication types

  • Comparative Study

MeSH terms

  • Adrenalectomy
  • Aldosterone / pharmacology
  • Animals
  • Chemical Phenomena
  • Chemistry
  • Endometrium / drug effects
  • Endometrium / growth & development
  • Female
  • Male
  • Mineralocorticoid Receptor Antagonists / chemical synthesis*
  • Mineralocorticoid Receptor Antagonists / metabolism
  • Mineralocorticoid Receptor Antagonists / pharmacology
  • Molecular Structure
  • Potassium / urine
  • Pregnancy
  • Pregnancy Maintenance / drug effects
  • Rabbits
  • Rats
  • Rats, Inbred Strains
  • Receptors, Progesterone / metabolism
  • Sodium / urine
  • Spironolactone / analogs & derivatives*
  • Spironolactone / chemical synthesis
  • Spironolactone / metabolism
  • Spironolactone / pharmacology

Substances

  • Mineralocorticoid Receptor Antagonists
  • Receptors, Progesterone
  • 6,6-ethylene-15,16-methylene-3-oxo-17-pregn-4-ene-2,17-carbolactone
  • Spironolactone
  • Aldosterone
  • Sodium
  • Potassium