Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.
@article{Nickisch1987AldosteroneA2, title={Aldosterone antagonists. 2. New 7 alpha-(acetylthio)-15,16-methylene spirolactones.}, author={Klaus Nickisch and Dieter Bittler and Henry Laurent and Wolfgang Losert and Jorge Casals-stenzel and Yukishige Nishino and Ekkehardt Schillinger and Rudolf Prof. Dr. Wiechert}, journal={Journal of medicinal chemistry}, year={1987}, volume={30 8}, pages={ 1403-9 } }
Some 15,16-methylene derivatives of the aldosterone antagonist spironolactone were synthesized with the purpose of increasing the antialdosterone potency and reducing the endocrinological effects of this standard compound. By introduction of a 1,2-double bond and a 15 beta,16 beta-methylene ring in the spironolactone molecule both goals were achieved. In animal studies mespirenone exhibited a threefold-greater antialdosterone potency and less than 10% of the antiandrogenic activity of…
20 Citations
Synthesis of new steroidal 11β-substituted spirolactones
- Chemistry
- 1990
A stereoselective synthesis of new 3-oxo-11β-(3-alkoxypropyl)-19-nor-17α-pregna-4,9-diene-21,17-carbolactones has been achieved. The purpose of this study was to synthesize new 11β-substituted…
Discovery of a subnanomolar and selective spirocyclic agonist of the glucocorticoid receptor.
- Chemistry, BiologyEuropean journal of medicinal chemistry
- 2019
Investigation of structure-activity relationship on 17-spirolactone derivatives: the electronic-topological approach.
- Chemistry, BiologyFarmaco
- 2002
Intramolecular condensation of steroidal 17α-formyl 17β-acetates: synthesis of 14-functionalised 17-spirolactones
- Chemistry
- 1990
Variable mapping of structure-activity relationships: application to 17-spirolactone derivatives with mineralocorticoid activity.
- ChemistryJournal of molecular graphics
- 1995
Synthesis of the fatty sterol bound protein for a new sterol antibody.
- Chemistry, BiologyBioorganic & medicinal chemistry letters
- 2000
Corticosteroid receptor antagonists: A current perspective
- Biology, MedicinePharmacy World and Science
- 2005
This review aims to highlight a selection of antagonists for the mineraloc Corticoid and glucocorticoid receptors, together with their pharmacological profiles and, when appropriate, clinical and therapeutic applications.
Steroidal cyclobutanones. IV: Heterocyclic spiroannulation of 5α-cholestan-3-one. Stereospecific Beckmann rearrangement of steroidal 3-spirocyclobutanone oximes
- Chemistry
- 1993
Diastereomeric 5α-cholestane-3,3′-spiro-2′,2′-dichlorocyclobutanones 1 and 2 served as starting materials for the synthesis of related heterocyclic spirane derivatives. Thus, diastereomeric…
Antialdosterones: incidence and prevention of sexual side effects.
- Medicine, BiologyJournal of steroid biochemistry
- 1989
Steroidal cyclobutanones, V. the baeyer‐villiger rearrangement of α‐substituted β‐spirocyclobutanones
- Chemistry
- 1995
The reaction of the steroidal spiro-α,α-dichlorocyclobutanone 1 carried out in basic H2O2/MeOH/THF solution proceeds with cine substitution leading to the intermediate α-chloro-α-methoxycyclobutanone…