Science and Technology Production
Article
Authorship
DANSEY, MARIA VIRGINIA
;
Di Chenna, Pablo Hector
;
Veleiro, Adriana S.
;
Kritofíková, Z
;
Chodounska, H.
;
Kasal, A.
;
Burton, Gerardo
Date
2010
Publishing House and Editing Place
Elsevier
Magazine
EUROPEAN JOURNAL OF MEDICAL CHEMISTRY,
vol. 45
(pp. 3063-3069)
Elsevier
Summary
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SIGEVA
A procedure is described for the preparation of A-homo-5-pregnenes via an acid catalyzed rearrangement of cyclopropylcarbinols assisted by microwave irradiation. 3á-Hydroxy and 4á-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 a...
A procedure is described for the preparation of A-homo-5-pregnenes via an acid catalyzed rearrangement of cyclopropylcarbinols assisted by microwave irradiation. 3á-Hydroxy and 4á-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, 3â-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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Key Words
A-homopregnanegAminobutyric acidNeurosteroidGABAA receptor