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Abstract:

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. © 2006 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone
Autor:Durán, F.J.; Ghini, A.A.; Coirini, H.; Burton, G.
Filiación:Departamento de Química Orgánica and UMYMFOR (CONICET-FCEN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellon 2, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina
Instituto de Biología y Medicina Experimental (CONICET), Vuelta de Obligado 2490, C1428ADN Buenos Aires, Argentina
Palabras clave:6-Thiasteroids; Allopregnanolone; GABAA receptor; Neurosteroid analogs; S,S-Dioxo-thiasteroids; S-Oxo-thiasteroids; 3alpha benzyloxy 19 hydroxy 6 thia 5alpha pregnan 20 one; 3alpha hydroxy 5alpha pregnan 20 one; 3alpha hydroxy 6 thia 5alpha pregnan 20 one; 3beta hydroxy 19 formyloxy 6 thia 5alpha pregnan 20 one; neurosteroid; pregnane derivative; sulfone derivative; sulfoxide; unclassified drug; analytic method; animal tissue; article; chemical bond; chemical procedures; chemical reaction; controlled study; drug receptor binding; drug synthesis; ligand binding; male; nonhuman; priority journal; rat; reaction analysis; stereochemistry; Animalia; Thia
Año:2006
Volumen:62
Número:20
Página de inicio:4762
Página de fin:4768
DOI: http://dx.doi.org/10.1016/j.tet.2006.03.025
Título revista:Tetrahedron
Título revista abreviado:Tetrahedron
ISSN:00404020
CODEN:TETRA
CAS:3alpha hydroxy 5alpha pregnan 20 one, 516-54-1; sulfoxide, 120-62-7
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v62_n20_p4762_Duran

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Citas:

---------- APA ----------
Durán, F.J., Ghini, A.A., Coirini, H. & Burton, G. (2006) . Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone. Tetrahedron, 62(20), 4762-4768.
http://dx.doi.org/10.1016/j.tet.2006.03.025
---------- CHICAGO ----------
Durán, F.J., Ghini, A.A., Coirini, H., Burton, G. "Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone" . Tetrahedron 62, no. 20 (2006) : 4762-4768.
http://dx.doi.org/10.1016/j.tet.2006.03.025
---------- MLA ----------
Durán, F.J., Ghini, A.A., Coirini, H., Burton, G. "Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone" . Tetrahedron, vol. 62, no. 20, 2006, pp. 4762-4768.
http://dx.doi.org/10.1016/j.tet.2006.03.025
---------- VANCOUVER ----------
Durán, F.J., Ghini, A.A., Coirini, H., Burton, G. Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone. Tetrahedron. 2006;62(20):4762-4768.
http://dx.doi.org/10.1016/j.tet.2006.03.025