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- W2131569781 abstract "A procedure is described for the preparation of A-homo-5-pregnenes via an acid catalyzed rearrangement of cyclopropylcarbinols assisted by microwave irradiation. 3α-Hydroxy and 4α-hydroxy-A-homo-5-pregnen-20-one, analogues of the neuroactive steroid allopregnanolone, were obtained by means of a regioselective epoxidation of a double bond in the expanded A-ring, using a fructose-derived chiral ketone as catalyst and oxone as oxidant. Although both these compounds were marginally active in inhibiting TBPS binding to GABAA receptors, 3β-hydroxy-A-homo-5-pregnen-20-one was almost as active as allopregnanolone. Reduction of the double bond of the latter compound resulted in a ten fold loss of activity." @default.
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- W2131569781 date "2010-07-01" @default.
- W2131569781 modified "2023-10-15" @default.
- W2131569781 title "Synthesis and GABAA receptor activity of A-homo analogues of neuroactive steroids" @default.
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- W2131569781 doi "https://doi.org/10.1016/j.ejmech.2010.03.037" @default.
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