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Abstract:

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.

Registro:

Documento: Artículo
Título:Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids
Autor:Martínez, M.D.; Edelsztein, V.C.; Durán, F.J.; Di Chenna, P.H.; Burton, G.
Filiación:Departamento de Química Orgánica and UMYMFOR (CONICET-UBA), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, C1428EGA Buenos Aires, Argentina
Palabras clave: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
Año:2013
Volumen:78
Número:1
Página de inicio:34
Página de fin:37
DOI: http://dx.doi.org/10.1016/j.steroids.2012.10.012
Título revista:Steroids
Título revista abreviado:Steroids
ISSN:0039128X
CODEN:STEDA
CAS:18 hydroxydeoxycorticosterone, 379-68-0; 18 hydroxyprogesterone, 596-69-0; manganese dioxide, 1313-13-9; pregnenolone, 145-13-1; 6-azaprogesterone; Luciferases, 1.13.12.-; Pregnanes; Progesterone, 57-83-0; Receptors, Progesterone
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_0039128X_v78_n1_p34_Martinez

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Citas:

---------- APA ----------
Martínez, M.D., Edelsztein, V.C., Durán, F.J., Di Chenna, P.H. & Burton, G. (2013) . Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids. Steroids, 78(1), 34-37.
http://dx.doi.org/10.1016/j.steroids.2012.10.012
---------- CHICAGO ----------
Martínez, M.D., Edelsztein, V.C., Durán, F.J., Di Chenna, P.H., Burton, G. "Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids" . Steroids 78, no. 1 (2013) : 34-37.
http://dx.doi.org/10.1016/j.steroids.2012.10.012
---------- MLA ----------
Martínez, M.D., Edelsztein, V.C., Durán, F.J., Di Chenna, P.H., Burton, G. "Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids" . Steroids, vol. 78, no. 1, 2013, pp. 34-37.
http://dx.doi.org/10.1016/j.steroids.2012.10.012
---------- VANCOUVER ----------
Martínez, M.D., Edelsztein, V.C., Durán, F.J., Di Chenna, P.H., Burton, G. Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids. Steroids. 2013;78(1):34-37.
http://dx.doi.org/10.1016/j.steroids.2012.10.012