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:	Martínez, M.D., Edelsztein, V.C., Durán, F.J., Di Chenna, P.H., Burton, G.
Formato:	JOUR
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:	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

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spelling	todo:paper_0039128X_v78_n1_p34_Martinez2023-10-03T14:49:31Z Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids Martínez, M.D. Edelsztein, V.C. Durán, F.J. Di Chenna, P.H. Burton, G. 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. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar 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 Martínez, M.D. Edelsztein, V.C. Durán, F.J. Di Chenna, P.H. Burton, G. 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.
format	JOUR
author	Martínez, M.D. Edelsztein, V.C. Durán, F.J. Di Chenna, P.H. Burton, G.
author_facet	Martínez, M.D. Edelsztein, V.C. Durán, F.J. Di Chenna, P.H. Burton, G.
author_sort	Martínez, M.D.
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
url	http://hdl.handle.net/20.500.12110/paper_0039128X_v78_n1_p34_Martinez
work_keys_str_mv	AT martinezmd synthesisof6azaprogesteroneand19hydroxy6azasteroids AT edelszteinvc synthesisof6azaprogesteroneand19hydroxy6azasteroids AT duranfj synthesisof6azaprogesteroneand19hydroxy6azasteroids AT dichennaph synthesisof6azaprogesteroneand19hydroxy6azasteroids AT burtong synthesisof6azaprogesteroneand19hydroxy6azasteroids
_version_	1807323109479415808

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

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