AI Article Synopsis
- The text details a method for creating A-homo-5-pregnenes through an acid-catalyzed rearrangement of cyclopropylcarbinols with microwave assistance.
- The process includes making specific hydroxy analogues of a neuroactive steroid called allopregnanolone using a chiral ketone and an oxidizing agent.
- While the new compounds showed some activity in inhibiting a specific receptor, one particular compound maintained a strong activity similar to allopregnanolone, but reducing its double bond significantly decreased its effectiveness.
Article Abstract
A procedure is described for the preparation of A-homo-5-pregnenes via an acid catalyzed rearrangement of cyclopropylcarbinols assisted by microwave irradiation. 3alpha-Hydroxy and 4alpha-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 GABA(A) receptors, 3beta-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.
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| http://dx.doi.org/10.1016/j.ejmech.2010.03.037 | DOI Listing |
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