Suppressing aggressive behavior with analogs of allopregnanolone (epalon)

3α-Hydroxy-20-oxo-5α-pregnan-21-yl hemisuccinate ( 8) was produced by partial acylation of 3α,21-dihydroxy-5α-pregnan-20-one ( 14). 3α-Fluoro-5α-pregnan-20-one ( 9) was prepared by treatment of 3β-hydroxy-5α-pregnan-20-one ( 11) with DAST and by solvolysis of tosylate 12 with tetrabutylammonium fluo...

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Bibliographic Details
Published in:Steroids 2001-02, Vol.66 (2), p.99-105
Main Authors: Slavı́ková, Barbora, Kasal, Alexander, Uhlı́řová, Leona, Kršiak, Miloslav, Chodounská, Hana, Kohout, Ladislav
Format: Article
Language:English
Subjects:
1H NMR spectroscopy
Aggression - drug effects
Allopregnanolone
Animals
Behavior
Biological and medical sciences
DAST
Diseases of eyelid, conjunctiva and lacrimal tracts
Epalon
GABA A-receptor
Male
Medical sciences
Mice
Mice, Inbred ICR
Ophthalmology
Pregnanolone - analogs & derivatives
Pregnanolone - pharmacology
Steroid
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Summary:3α-Hydroxy-20-oxo-5α-pregnan-21-yl hemisuccinate ( 8) was produced by partial acylation of 3α,21-dihydroxy-5α-pregnan-20-one ( 14). 3α-Fluoro-5α-pregnan-20-one ( 9) was prepared by treatment of 3β-hydroxy-5α-pregnan-20-one ( 11) with DAST and by solvolysis of tosylate 12 with tetrabutylammonium fluoride. A behavioral test on mice was performed using 3α-hydroxy-5α-pregnan-20-one ( 1) and compounds 8 and 9. Compound 8 was found to be inactive, while the fluoro derivative 9 selectively reduced aggressive behavior in mice more than the corresponding 3α-hydroxy compound 1; locomotion and other behavioral features were not affected.
ISSN:0039-128X
1878-5867
DOI:10.1016/S0039-128X(00)00215-4