UMYMFOR   05516
UNIDAD DE MICROANALISIS Y METODOS FISICOS EN QUIMICA ORGANICA
Unidad Ejecutora - UE
artículos
Título:
Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone
Autor/es:
F.J. DURÁN, A.A. GHINI, H. COIRINI AND G. BURTON
Revista:
TETRAHEDRON
Editorial:
Elsevier
Referencias:
Año: 2006 vol. 62 p. 4762 - 4768
ISSN:
0040-4020
Resumen:
A procedure is described for the preparation of 6-thiapregnanes in five steps from pregnenolone via a 5-oxo-7-iodo-secopregnane intermediate. The 6-thiasteroid obtained was converted into 6-thia-allopregnanolone and its sulfoxide and sulfone derivatives. The trans stereochemistry at the A/B ring junction was accomplished by stereoselective reduction of an intermediate hemithioketal with triethylsilane/BF3-Et2O. The compounds synthesized are analogs of natural neurosteroids, and exhibited GABAA receptor activity comparable to allopregnanolone.