Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone

Autores
Eduardo, S.L.; Ghini, A.A.; Burton, G.
Año de publicación
2003
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
3α-Hydroxy-2,19-oxido-5αH-pregnan-20-one was synthesized in 6 steps from the easily available 19-hydroxypregnenolone 3-acetate. The 2,19-oxido bridge was formed in a single step upon spontaneous cyclization and desilylation of a TBDMS protected 19-hydroxy-2α,3α-epoxypregnane. The 4,19-oxido analogue was obtained as a byproduct upon cyclization of the isomeric 3α,4α-epoxide.
Fil:Ghini, A.A. 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.
Fuente
Arkivoc 2003;2003(10):468-476
Materia
2,19-Oxido-allopregnanolone
4,19-oxido-allopregnanolone
Neurosteroid
Oxido-bridged steroid
19 hydroxy 2alpha,3alpha epoxypregnane
19 hydroxypregnenolone 3 acetate
3alpha hydroxy 2,19 oxido 5alphah pregnan 20 one
3alpha hydroxy 5alphah pregnan 20 one
4beta,19 oxido 3alpha hydroxy 5alphah pregnan 20 one
bridged compound
neurosteroid
silane derivative
unclassified drug
article
cyclization
desilylation
drug structure
drug synthesis
structure activity relation
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by/2.5/ar
Repositorio
Biblioteca Digital (UBA-FCEN)
Institución
Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturales
OAI Identificador
paperaa:paper_14246376_v2003_n10_p468_Eduardo
Acceder
id BDUBAFCEN_926305dd4c41110a99c235b6a0332846
oai_identifier_str paperaa:paper_14246376_v2003_n10_p468_Eduardo
network_acronym_str BDUBAFCEN
repository_id_str 1896
network_name_str Biblioteca Digital (UBA-FCEN)
spelling Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanoloneEduardo, S.L.Ghini, A.A.Burton, G.2,19-Oxido-allopregnanolone4,19-oxido-allopregnanoloneNeurosteroidOxido-bridged steroid19 hydroxy 2alpha,3alpha epoxypregnane19 hydroxypregnenolone 3 acetate3alpha hydroxy 2,19 oxido 5alphah pregnan 20 one3alpha hydroxy 5alphah pregnan 20 one4beta,19 oxido 3alpha hydroxy 5alphah pregnan 20 onebridged compoundneurosteroidsilane derivativeunclassified drugarticlecyclizationdesilylationdrug structuredrug synthesisstructure activity relation3α-Hydroxy-2,19-oxido-5αH-pregnan-20-one was synthesized in 6 steps from the easily available 19-hydroxypregnenolone 3-acetate. The 2,19-oxido bridge was formed in a single step upon spontaneous cyclization and desilylation of a TBDMS protected 19-hydroxy-2α,3α-epoxypregnane. The 4,19-oxido analogue was obtained as a byproduct upon cyclization of the isomeric 3α,4α-epoxide.Fil:Ghini, A.A. 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.2003info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfhttp://hdl.handle.net/20.500.12110/paper_14246376_v2003_n10_p468_EduardoArkivoc 2003;2003(10):468-476reponame:Biblioteca Digital (UBA-FCEN)instname:Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturalesinstacron:UBA-FCENenginfo:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/2.5/ar2025-09-04T09:48:28Zpaperaa:paper_14246376_v2003_n10_p468_EduardoInstitucionalhttps://digital.bl.fcen.uba.ar/Universidad públicaNo correspondehttps://digital.bl.fcen.uba.ar/cgi-bin/oaiserver.cgiana@bl.fcen.uba.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:18962025-09-04 09:48:32.973Biblioteca Digital (UBA-FCEN) - Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturalesfalse
dc.title.none.fl_str_mv Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone
title Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone
spellingShingle Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone
Eduardo, S.L.
2,19-Oxido-allopregnanolone
4,19-oxido-allopregnanolone
Neurosteroid
Oxido-bridged steroid
19 hydroxy 2alpha,3alpha epoxypregnane
19 hydroxypregnenolone 3 acetate
3alpha hydroxy 2,19 oxido 5alphah pregnan 20 one
3alpha hydroxy 5alphah pregnan 20 one
4beta,19 oxido 3alpha hydroxy 5alphah pregnan 20 one
bridged compound
neurosteroid
silane derivative
unclassified drug
article
cyclization
desilylation
drug structure
drug synthesis
structure activity relation
title_short Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone
title_full Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone
title_fullStr Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone
title_full_unstemmed Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone
title_sort Oxido-bridged neurosteroid analogues. Synthesis of 2,19-oxido-allopregnanolone
dc.creator.none.fl_str_mv Eduardo, S.L.
Ghini, A.A.
Burton, G.
author Eduardo, S.L.
author_facet Eduardo, S.L.
Ghini, A.A.
Burton, G.
author_role author
author2 Ghini, A.A.
Burton, G.
author2_role author
author
dc.subject.none.fl_str_mv 2,19-Oxido-allopregnanolone
4,19-oxido-allopregnanolone
Neurosteroid
Oxido-bridged steroid
19 hydroxy 2alpha,3alpha epoxypregnane
19 hydroxypregnenolone 3 acetate
3alpha hydroxy 2,19 oxido 5alphah pregnan 20 one
3alpha hydroxy 5alphah pregnan 20 one
4beta,19 oxido 3alpha hydroxy 5alphah pregnan 20 one
bridged compound
neurosteroid
silane derivative
unclassified drug
article
cyclization
desilylation
drug structure
drug synthesis
structure activity relation
topic 2,19-Oxido-allopregnanolone
4,19-oxido-allopregnanolone
Neurosteroid
Oxido-bridged steroid
19 hydroxy 2alpha,3alpha epoxypregnane
19 hydroxypregnenolone 3 acetate
3alpha hydroxy 2,19 oxido 5alphah pregnan 20 one
3alpha hydroxy 5alphah pregnan 20 one
4beta,19 oxido 3alpha hydroxy 5alphah pregnan 20 one
bridged compound
neurosteroid
silane derivative
unclassified drug
article
cyclization
desilylation
drug structure
drug synthesis
structure activity relation
dc.description.none.fl_txt_mv 3α-Hydroxy-2,19-oxido-5αH-pregnan-20-one was synthesized in 6 steps from the easily available 19-hydroxypregnenolone 3-acetate. The 2,19-oxido bridge was formed in a single step upon spontaneous cyclization and desilylation of a TBDMS protected 19-hydroxy-2α,3α-epoxypregnane. The 4,19-oxido analogue was obtained as a byproduct upon cyclization of the isomeric 3α,4α-epoxide.
Fil:Ghini, A.A. 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.
description 3α-Hydroxy-2,19-oxido-5αH-pregnan-20-one was synthesized in 6 steps from the easily available 19-hydroxypregnenolone 3-acetate. The 2,19-oxido bridge was formed in a single step upon spontaneous cyclization and desilylation of a TBDMS protected 19-hydroxy-2α,3α-epoxypregnane. The 4,19-oxido analogue was obtained as a byproduct upon cyclization of the isomeric 3α,4α-epoxide.
publishDate 2003
dc.date.none.fl_str_mv 2003
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/20.500.12110/paper_14246376_v2003_n10_p468_Eduardo
url http://hdl.handle.net/20.500.12110/paper_14246376_v2003_n10_p468_Eduardo
dc.language.none.fl_str_mv eng
language eng
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/2.5/ar
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/2.5/ar
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv Arkivoc 2003;2003(10):468-476
reponame:Biblioteca Digital (UBA-FCEN)
instname:Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturales
instacron:UBA-FCEN
reponame_str Biblioteca Digital (UBA-FCEN)
collection Biblioteca Digital (UBA-FCEN)
instname_str Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturales
instacron_str UBA-FCEN
institution UBA-FCEN
repository.name.fl_str_mv Biblioteca Digital (UBA-FCEN) - Universidad Nacional de Buenos Aires. Facultad de Ciencias Exactas y Naturales
repository.mail.fl_str_mv ana@bl.fcen.uba.ar
_version_ 1842340703670108160
score 12.623145

Publicaciones similares