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Allopregnanolone and pregnanolone analogues modified in the C ring: Synthesis and activity

AuthorsSlavíková, Barbora; Bujons Vilàs, Jordi ; Matyáš, Libor; Vidal, Miguel ; Babot, Zoila ; Krištofíková, Zdena; Suñol, Cristina ; Kasal, Alexander
Issue Date2013
PublisherAmerican Chemical Society
CitationJournal of Medicinal Chemistry 56(6): 2323-2336 (2013)
Abstract(25R)-3β-Hydroxy-5α-spirostan-12-one (hecogenin) and 11α-hydroxypregn-4-ene-3,20-dione (11α-hydroxyprogesterone) were used as starting materials for the synthesis of a series of 11- and 12-substituted derivatives of 5ξ-pregnanolone (3α-hydroxy-5α- pregnan-20-one and 3α-hydroxy-5β-pregnan-20-one), the principal neurosteroid acting via γ-aminobutyric acid (GABA). These analogues were designed to study the structural requirements of the corresponding GABA A receptor. Their biological activity was measured by in vitro test with [3H]flunitrazepam as radioligand in which allopregnanolone and its active analogues stimulated the binding to the GABAA receptor. Analysis of the SAR data suggests dependence of the flunitrazepam binding activity on the hydrophobic-hydrophilic balance of the groups at the C-ring edge rather than on specific interactions between them and the receptor. © 2013 American Chemical Society.
DescriptionEl pdf es la versión post-print.
Publisher version (URL)http://dx.doi.org/10.1021/jm3016365
Identifiersdoi: 10.1021/jm3016365
issn: 0022-2623
e-issn: 1520-4804
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