Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone

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 jun...

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Autores principales:	Durán, F.J., Ghini, A.A., Coirini, H., Burton, G.
Formato:	JOUR
Materias:	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
Acceso en línea:	http://hdl.handle.net/20.500.12110/paper_00404020_v62_n20_p4762_Duran
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

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spelling	todo:paper_00404020_v62_n20_p4762_Duran2023-10-03T14:50:42Z Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone Durán, F.J. Ghini, A.A. Coirini, H. Burton, G. 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 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. Fil:Durán, F.J. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ghini, A.A. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Coirini, H. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_00404020_v62_n20_p4762_Duran
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	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
spellingShingle	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 Durán, F.J. Ghini, A.A. Coirini, H. Burton, G. Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone
topic_facet	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
description	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.
format	JOUR
author	Durán, F.J. Ghini, A.A. Coirini, H. Burton, G.
author_facet	Durán, F.J. Ghini, A.A. Coirini, H. Burton, G.
author_sort	Durán, F.J.
title	Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone
title_short	Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone
title_full	Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone
title_fullStr	Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone
title_full_unstemmed	Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone
title_sort	synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone
url	http://hdl.handle.net/20.500.12110/paper_00404020_v62_n20_p4762_Duran
work_keys_str_mv	AT duranfj synthesisof6thiaanalogsofthenaturalneurosteroidallopregnanolone AT ghiniaa synthesisof6thiaanalogsofthenaturalneurosteroidallopregnanolone AT coirinih synthesisof6thiaanalogsofthenaturalneurosteroidallopregnanolone AT burtong synthesisof6thiaanalogsofthenaturalneurosteroidallopregnanolone
_version_	1807324410375307264

Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone

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