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...
| Autores principales: | , , , |
|---|---|
| Publicado: |
2006
|
| Materias: | |
| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v62_n20_p4762_Duran http://hdl.handle.net/20.500.12110/paper_00404020_v62_n20_p4762_Duran |
| Aporte de: |
| id |
paper:paper_00404020_v62_n20_p4762_Duran |
|---|---|
| record_format |
dspace |
| spelling |
paper:paper_00404020_v62_n20_p4762_Duran2023-06-08T15:04:16Z Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone Durán, Fernando Javier Ghini, Alberto Antonio Coirini, Héctor Burton, Gerardo 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. 2006 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v62_n20_p4762_Duran 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, Fernando Javier Ghini, Alberto Antonio Coirini, Héctor Burton, Gerardo 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. |
| author |
Durán, Fernando Javier Ghini, Alberto Antonio Coirini, Héctor Burton, Gerardo |
| author_facet |
Durán, Fernando Javier Ghini, Alberto Antonio Coirini, Héctor Burton, Gerardo |
| author_sort |
Durán, Fernando Javier |
| 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 |
| publishDate |
2006 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00404020_v62_n20_p4762_Duran http://hdl.handle.net/20.500.12110/paper_00404020_v62_n20_p4762_Duran |
| work_keys_str_mv |
AT duranfernandojavier synthesisof6thiaanalogsofthenaturalneurosteroidallopregnanolone AT ghinialbertoantonio synthesisof6thiaanalogsofthenaturalneurosteroidallopregnanolone AT coirinihector synthesisof6thiaanalogsofthenaturalneurosteroidallopregnanolone AT burtongerardo synthesisof6thiaanalogsofthenaturalneurosteroidallopregnanolone |
| _version_ |
1768545919041536000 |