Aldosterone antagonists. 3. Synthesis and activities of steroidal 7 alpha-(alkoxycarbonyl)-15,16-methylene spirolactones

Several A- and D-ring substituted steroidal 7 alpha-alkoxycarbonyl spirolactones were synthesized with the purpose of increasing the aldosterone antagonistic potency and reducing the endocrinological side effects relative to the standard drug spironolactone. It was found that the 15 beta,16 beta-met...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Journal of medicinal chemistry 1990-02, Vol.33 (2), p.509-513
Hauptverfasser:	Nickisch, K, Bittler, D, Laurent, H, Losert, W, Nishino, Y, Schillinger, E, Wiechert, R
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Biological Assay Chemical Phenomena Chemistry Female Male Mineralocorticoid Receptor Antagonists - chemical synthesis Mineralocorticoid Receptor Antagonists - metabolism Orchiectomy Ovulation - drug effects Pregnadienes - chemical synthesis Pregnadienes - pharmacology Pregnancy Rabbits Rats Rats, Inbred Strains Receptors, Androgen - metabolism Receptors, Progesterone - metabolism Spironolactone - analogs & derivatives Spironolactone - chemical synthesis Spironolactone - pharmacology Structure-Activity Relationship
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	Several A- and D-ring substituted steroidal 7 alpha-alkoxycarbonyl spirolactones were synthesized with the purpose of increasing the aldosterone antagonistic potency and reducing the endocrinological side effects relative to the standard drug spironolactone. It was found that the 15 beta,16 beta-methylene derivative 17 exhibited a 2-fold higher aldosterone antagonistic activity compared to either spironolactone or the 15,16-unsubstituted derivative 29 while showing remarkably reduced antiandrogenicity.
ISSN:	0022-2623
DOI:	10.1021/jm00164a007