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Many different 3α-hydroxysteroids in the androstane and pregnane steroid series enhance the actions of γ-aminobutyric acid (GABA) at GABA type-A (GABA A ) receptors in the mammalian central nervous system. Recent studies have shown that (3α,5α)-3-hydroxyandrostan-17-one (androsterone) is less active at these receptors than its enantiomer ent-androsterone. Further structure–activity relationship...
The synthesis of 18-nor-Δ 13(17) -androgens and the structurally related 13,17-epoxides is described. The synthetic route involves the cleavage of 17-ketosteroids by an abnormal Beckmann rearrangement, modification of the D-ring cleavage product to obtain an intermediate tricyclic diene and ring closing metathesis of the diene to the 18-nor-Δ 13(17) -androgen. (3α,5α)-18-Norandrost-13(17)-en-3-ol...
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