title: [Acetylation of spironolactone, canrenone and 2-methyl-canrenone].
abstract: Reaction of the title compounds with acetic anhydride and acetyl chloride yields the 3,5-dien-3-yl acetate 2, the isomeric 2,4,6- and 3,5,7-trien-3-yl acetates 3 and 4 as well as the 2,4,6,8(14)-tetraen-3-yl acetate 7. The 2 alpha-methyl-8,14-didehydro-canrenone (9) is obtained by hydrolysis of 7. Binding affinities of 7 and 9 to hormone receptors as well as serum proteins (SHBG, CBG) are investigated. The compounds are inactive.
authors.affiliation: Institut für Pharmazeutische Chemie, Technischen Universität Braunschweig.
authors.forename: K
authors.initials: K
authors.lastname: Görlitzer
authors.forename: P
authors.initials: P
authors.lastname: Moormann
authors.forename: K
authors.initials: K
authors.lastname: Pollow
authors.forename: M
authors.initials: M
authors.lastname: Schaffrath
mesh_terms: D000107:Acetylation; D000818:Animals; D001667:Binding, Competitive / Q000187:drug effects; D001798:Blood Proteins / Q000378:metabolism; D002192:Canrenone / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000493:pharmacokinetics; D006801:Humans; D066298:In Vitro Techniques; D051381:Rats; D017208:Rats, Wistar; D011956:Receptors, Cell Surface / Q000378:metabolism; D013148:Spironolactone / Q000737:chemistry* / Q000493:pharmacokinetics
chemical_list: C093222:2-methylenecanrenone; D001798:Blood Proteins; D011956:Receptors, Cell Surface; D013148:Spironolactone; D002192:Canrenone
vernacular_title: Zur Acetylierung von Spironolacton, Canrenon und 2-Methylencanrenon.