Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids

19-Hydroxy-6-azapregnanes were obtained from pregnenolone via a 7-azido-5-oxo-6-nor-5,7-secopregnane intermediate. The 6-azapregnane core was built in good yield in a straightforward way from the secosteroid, by means of a Staudinger (aza-Wittig) reaction. Finally the 19-hydroxy-6-azapregnane was tr...

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Autores principales:	Edelsztein, Valeria Carolina, Durán, Fernando Javier, Di Chenna, Pablo Héctor, Burton, Gerardo
Publicado:	2013
Materias:	19-Hydroxypregnane 6-Azaprogesterone Azasteroids Gestagenic activity 18 hydroxy 20 oxosteroid 18 hydroxydeoxycorticosterone 18 hydroxyprogesterone 19 hydroxy 3 oxosteroid 19 hydroxy 6 (tert butoxycarbonyl) 6 aza 4 pregnene 3,20 dione 19 hydroxy 6 azaprogesterone 19 hydroxy 6 azasteroid 3beta tert butyldimethylsilyloxy 19 formyloxy 6 aza 5 pregnen 20 one 3beta tert butyldimethylsilyloxy 6 (tert butoxycarbonyl) 19 formyloxy 6 aza 4 pregnen 20 one 3beta tert butyldimethylsilyloxy 7 azido 19 formyloxy 6 nor 5,7 secopregnane 5,20 dione 3beta,19 dihydroxy 6 (tert butoxycarbonyl) 6 aza 4 pregnen 20 one 6 azaprogesterone azasteroid gestagen manganese dioxide pregnenolone progesterone receptor secosteroid unclassified drug acylation animal cell article chemical bond controlled study cyclization drug structure drug synthesis human nonhuman reduction structure activity relation Animals Cercopithecus aethiops COS Cells Cyclization Gene Expression Genes, Reporter Humans Luciferases Pregnanes Progesterone Promoter Regions, Genetic Receptors, Progesterone
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v78_n1_p34_Martinez http://hdl.handle.net/20.500.12110/paper_0039128X_v78_n1_p34_Martinez
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_0039128X_v78_n1_p34_Martinez
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spelling	paper:paper_0039128X_v78_n1_p34_Martinez2023-06-08T15:03:22Z Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids Edelsztein, Valeria Carolina Durán, Fernando Javier Di Chenna, Pablo Héctor Burton, Gerardo 19-Hydroxypregnane 6-Azaprogesterone Azasteroids Gestagenic activity 18 hydroxy 20 oxosteroid 18 hydroxydeoxycorticosterone 18 hydroxyprogesterone 19 hydroxy 3 oxosteroid 19 hydroxy 6 (tert butoxycarbonyl) 6 aza 4 pregnene 3,20 dione 19 hydroxy 6 azaprogesterone 19 hydroxy 6 azasteroid 3beta tert butyldimethylsilyloxy 19 formyloxy 6 aza 5 pregnen 20 one 3beta tert butyldimethylsilyloxy 6 (tert butoxycarbonyl) 19 formyloxy 6 aza 4 pregnen 20 one 3beta tert butyldimethylsilyloxy 7 azido 19 formyloxy 6 nor 5,7 secopregnane 5,20 dione 3beta,19 dihydroxy 6 (tert butoxycarbonyl) 6 aza 4 pregnen 20 one 6 azaprogesterone azasteroid gestagen manganese dioxide pregnenolone progesterone receptor secosteroid unclassified drug acylation animal cell article chemical bond controlled study cyclization drug structure drug synthesis human nonhuman reduction structure activity relation Animals Cercopithecus aethiops COS Cells Cyclization Gene Expression Genes, Reporter Humans Luciferases Pregnanes Progesterone Promoter Regions, Genetic Receptors, Progesterone 19-Hydroxy-6-azapregnanes were obtained from pregnenolone via a 7-azido-5-oxo-6-nor-5,7-secopregnane intermediate. The 6-azapregnane core was built in good yield in a straightforward way from the secosteroid, by means of a Staudinger (aza-Wittig) reaction. Finally the 19-hydroxy-6-azapregnane was transformed into 19-hydroxy-6-azaprogesterone (that cyclized spontaneously to the 19 → 3 hemiketal) and 6-azaprogesterone. The 6-azapregnanes lacked agonistic/antagonistic activity on the progesterone receptor. © 2012 Elsevier Inc. All rights reserved. Fil:Edelsztein, V.C. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Durán, F.J. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Di Chenna, P.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. 2013 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v78_n1_p34_Martinez http://hdl.handle.net/20.500.12110/paper_0039128X_v78_n1_p34_Martinez
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	19-Hydroxypregnane 6-Azaprogesterone Azasteroids Gestagenic activity 18 hydroxy 20 oxosteroid 18 hydroxydeoxycorticosterone 18 hydroxyprogesterone 19 hydroxy 3 oxosteroid 19 hydroxy 6 (tert butoxycarbonyl) 6 aza 4 pregnene 3,20 dione 19 hydroxy 6 azaprogesterone 19 hydroxy 6 azasteroid 3beta tert butyldimethylsilyloxy 19 formyloxy 6 aza 5 pregnen 20 one 3beta tert butyldimethylsilyloxy 6 (tert butoxycarbonyl) 19 formyloxy 6 aza 4 pregnen 20 one 3beta tert butyldimethylsilyloxy 7 azido 19 formyloxy 6 nor 5,7 secopregnane 5,20 dione 3beta,19 dihydroxy 6 (tert butoxycarbonyl) 6 aza 4 pregnen 20 one 6 azaprogesterone azasteroid gestagen manganese dioxide pregnenolone progesterone receptor secosteroid unclassified drug acylation animal cell article chemical bond controlled study cyclization drug structure drug synthesis human nonhuman reduction structure activity relation Animals Cercopithecus aethiops COS Cells Cyclization Gene Expression Genes, Reporter Humans Luciferases Pregnanes Progesterone Promoter Regions, Genetic Receptors, Progesterone
spellingShingle	19-Hydroxypregnane 6-Azaprogesterone Azasteroids Gestagenic activity 18 hydroxy 20 oxosteroid 18 hydroxydeoxycorticosterone 18 hydroxyprogesterone 19 hydroxy 3 oxosteroid 19 hydroxy 6 (tert butoxycarbonyl) 6 aza 4 pregnene 3,20 dione 19 hydroxy 6 azaprogesterone 19 hydroxy 6 azasteroid 3beta tert butyldimethylsilyloxy 19 formyloxy 6 aza 5 pregnen 20 one 3beta tert butyldimethylsilyloxy 6 (tert butoxycarbonyl) 19 formyloxy 6 aza 4 pregnen 20 one 3beta tert butyldimethylsilyloxy 7 azido 19 formyloxy 6 nor 5,7 secopregnane 5,20 dione 3beta,19 dihydroxy 6 (tert butoxycarbonyl) 6 aza 4 pregnen 20 one 6 azaprogesterone azasteroid gestagen manganese dioxide pregnenolone progesterone receptor secosteroid unclassified drug acylation animal cell article chemical bond controlled study cyclization drug structure drug synthesis human nonhuman reduction structure activity relation Animals Cercopithecus aethiops COS Cells Cyclization Gene Expression Genes, Reporter Humans Luciferases Pregnanes Progesterone Promoter Regions, Genetic Receptors, Progesterone Edelsztein, Valeria Carolina Durán, Fernando Javier Di Chenna, Pablo Héctor Burton, Gerardo Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids
topic_facet	19-Hydroxypregnane 6-Azaprogesterone Azasteroids Gestagenic activity 18 hydroxy 20 oxosteroid 18 hydroxydeoxycorticosterone 18 hydroxyprogesterone 19 hydroxy 3 oxosteroid 19 hydroxy 6 (tert butoxycarbonyl) 6 aza 4 pregnene 3,20 dione 19 hydroxy 6 azaprogesterone 19 hydroxy 6 azasteroid 3beta tert butyldimethylsilyloxy 19 formyloxy 6 aza 5 pregnen 20 one 3beta tert butyldimethylsilyloxy 6 (tert butoxycarbonyl) 19 formyloxy 6 aza 4 pregnen 20 one 3beta tert butyldimethylsilyloxy 7 azido 19 formyloxy 6 nor 5,7 secopregnane 5,20 dione 3beta,19 dihydroxy 6 (tert butoxycarbonyl) 6 aza 4 pregnen 20 one 6 azaprogesterone azasteroid gestagen manganese dioxide pregnenolone progesterone receptor secosteroid unclassified drug acylation animal cell article chemical bond controlled study cyclization drug structure drug synthesis human nonhuman reduction structure activity relation Animals Cercopithecus aethiops COS Cells Cyclization Gene Expression Genes, Reporter Humans Luciferases Pregnanes Progesterone Promoter Regions, Genetic Receptors, Progesterone
description	19-Hydroxy-6-azapregnanes were obtained from pregnenolone via a 7-azido-5-oxo-6-nor-5,7-secopregnane intermediate. The 6-azapregnane core was built in good yield in a straightforward way from the secosteroid, by means of a Staudinger (aza-Wittig) reaction. Finally the 19-hydroxy-6-azapregnane was transformed into 19-hydroxy-6-azaprogesterone (that cyclized spontaneously to the 19 → 3 hemiketal) and 6-azaprogesterone. The 6-azapregnanes lacked agonistic/antagonistic activity on the progesterone receptor. © 2012 Elsevier Inc. All rights reserved.
author	Edelsztein, Valeria Carolina Durán, Fernando Javier Di Chenna, Pablo Héctor Burton, Gerardo
author_facet	Edelsztein, Valeria Carolina Durán, Fernando Javier Di Chenna, Pablo Héctor Burton, Gerardo
author_sort	Edelsztein, Valeria Carolina
title	Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids
title_short	Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids
title_full	Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids
title_fullStr	Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids
title_full_unstemmed	Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids
title_sort	synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids
publishDate	2013
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v78_n1_p34_Martinez http://hdl.handle.net/20.500.12110/paper_0039128X_v78_n1_p34_Martinez
work_keys_str_mv	AT edelszteinvaleriacarolina synthesisof6azaprogesteroneand19hydroxy6azasteroids AT duranfernandojavier synthesisof6azaprogesteroneand19hydroxy6azasteroids AT dichennapablohector synthesisof6azaprogesteroneand19hydroxy6azasteroids AT burtongerardo synthesisof6azaprogesteroneand19hydroxy6azasteroids
_version_	1768543984656842752

Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids

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