title: Synthesis of 6-azaprogesterone and 19-hydroxy-6-azasteroids.
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.
authors.affiliation: Departamento de Química Orgánica and UMYMFOR-CONICET-UBA, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina.
authors.forename: Mario D
authors.initials: MD
authors.lastname: Martínez
authors.forename: Valeria C
authors.initials: VC
authors.lastname: Edelsztein
authors.forename: Fernando J
authors.initials: FJ
authors.lastname: Durán
authors.forename: Pablo H
authors.initials: PH
authors.lastname: Di Chenna
authors.forename: Gerardo
authors.initials: G
authors.lastname: Burton
mesh_terms: D000818:Animals; D019556:COS Cells; D002522:Chlorocebus aethiops; D003500:Cyclization; D015870:Gene Expression / Q000187:drug effects; D017930:Genes, Reporter; D006801:Humans; D008156:Luciferases / Q000096:biosynthesis / Q000235:genetics; D011278:Pregnanes / Q000138:chemical synthesis* / Q000494:pharmacology; D011374:Progesterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D011401:Promoter Regions, Genetic; D011980:Receptors, Progesterone / Q000819:agonists / Q000037:antagonists & inhibitors
chemical_list: C581585:6-azaprogesterone; D011278:Pregnanes; D011980:Receptors, Progesterone; D011374:Progesterone; D008156:Luciferases