A safe and practical method for the preparation of 7α-thioether and thioester derivatives of spironolactone.
Spironolactone is a renal competitive aldosterone antagonist. One of its most important metabolite is the 7α-methylthio spironolactone: thus it is very important to have an efficient and safe access to this compound, for pharmacokinetic studies. In this context, we synthesized this metabolite by thioalkylation of 7α-thio spironolactone using Hünig's base with a very good yield. We also used our procedure to prepare, with an easy work-up and high yields, 7α-thioether and thioester derivatives of spironolactone, that could be useful for further Structure-Activity Relationships studies.
Université de Lyon, F-69622 Lyon, France.
Géraldine
G
Agusti
Sandrine
S
Bourgeois
Nathalie
N
Cartiser
Hatem
H
Fessi
Marc
M
Le Borgne
Thierry
T
Lomberget
D000097:Acetonitriles / Q000737:chemistry; D000478:Alkylation; D002853:Chromatography, Liquid; D004952:Esters; D055772:Green Chemistry Technology; D007783:Lactones / Q000138:chemical synthesis* / Q000302:isolation & purification; D012997:Solvents / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000302:isolation & purification
C581586:7alpha-methylthio spironolactone; D000097:Acetonitriles; D004952:Esters; D007783:Lactones; D012997:Solvents; D013141:Spiro Compounds; C032159:acetonitrile