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  • Allopregnanolone and pregnanolone analogues modified in the C ring: synthesis and activity.

Allopregnanolone and pregnanolone analogues modified in the C ring: synthesis and activity.

Journal of medicinal chemistry (2013-02-21)
Barbora Slavíková, Jordi Bujons, Libor Matyáš, Miguel Vidal, Zoila Babot, Zdena Krištofíková, Cristina Suñol, Alexander Kasal
要旨

(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 GABAA receptor. Their biological activity was measured by in vitro test with [(3)H]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.

材料
製品番号
ブランド
製品内容

Sigma-Aldrich
5α-プレグナン-3α-オール-20-オン, solid
カタログ番号
容量
在庫状況
単価
数量
Sigma-Aldrich
5β-プレグナン-3α-オール-20-オン
カタログ番号
容量
在庫状況
単価
数量