Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones

A procedure for the synthesis of 6,19-cyclopregnanes is described involving an intramolecular alkylation reaction of Δ4-3-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-hydro...

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Detalles Bibliográficos
Autores principales: Di Chenna, P.H., Veleiro, A.S., Sonego, J.M., Ceballos, N.R., Garland, M.T., Baggio, R.F., Burton, G.
Formato: JOUR
Materias:
Alkylation
Derivatives
Hormones
Synthesis (chemical)
Mineralocorticoid receptors
Uterus progesterone receptors
Organic compounds
Rattus
Acceso en línea:http://hdl.handle.net/20.500.12110/paper_14770520_v5_n15_p2453_DiChenna
Aporte de:
Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires
Descripción
Sumario:A procedure for the synthesis of 6,19-cyclopregnanes is described involving an intramolecular alkylation reaction of Δ4-3-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. © The Royal Society of Chemistry.

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