title: Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones.
abstract: A procedure for the synthesis of 6,19-cyclopregnanes is described involving an intramolecular alkylation reaction of Delta(4)-3-keto steroids with a 19-mesylate in the presence of KOH in isopropanol. Three 6,19-cyclopregnanes were prepared (4, 5 ,9); in the rat, 6,19-cycloprogesterone (4) and its 21-hydroxy derivative 5 displaced [3H]-dexamethasone from glucocorticoid receptors, the former compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors.
authors.affiliation: Departamento de Química Orgánica and UMYMFOR (CONICET-FCEN), Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria, C1428EGA Buenos Aires, Argentina.
authors.forename: Pablo H
authors.initials: PH
authors.lastname: Di Chenna
authors.forename: Adriana S
authors.initials: AS
authors.lastname: Veleiro
authors.forename: Juan M
authors.initials: JM
authors.lastname: Sonego
authors.forename: Nora R
authors.initials: NR
authors.lastname: Ceballos
authors.forename: M Teresa
authors.initials: MT
authors.lastname: Garland
authors.forename: Ricardo F
authors.initials: RF
authors.lastname: Baggio
authors.forename: Gerardo
authors.initials: G
authors.lastname: Burton
mesh_terms: D000818:Animals; D003500:Cyclization; D006728:Hormones / Q000138:chemical synthesis / Q000737:chemistry*; D007661:Ketoses / Q000737:chemistry; D008099:Liver / Q000187:drug effects / Q000378:metabolism; D008297:Male; D008958:Models, Molecular; D015394:Molecular Structure; D011278:Pregnanes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D051381:Rats; D017207:Rats, Sprague-Dawley; D011965:Receptors, Glucocorticoid / Q000378:metabolism; D013256:Steroids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D006728:Hormones; D007661:Ketoses; D011278:Pregnanes; D011965:Receptors, Glucocorticoid; D013256:Steroids