UMYMFOR 05516
UNIDAD DE MICROANALISIS Y METODOS FISICOS EN QUIMICA ORGANICA
Unidad Ejecutora - UE
artículos
Título:
Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones
Autor/es:
DI CHENNA, PABLO H.; VELEIRO, ADRIANA S.; SONEGO, JUAN M.; CEBALLOS, NORA R.; GARLAND, MARÍA T.; BAGGIO, RICARDO F.; BURTON, GERARDO
Revista:
Organic & Biomolecular Chemistry
Editorial:
Royal Society of Chemistry
Referencias:
Año: 2007 vol. 5 p. 2453 - 2457
ISSN:
1477-0520
Resumen:
A procedure for the synthesis of 6,19-cyclopregnanes is described involving an intramolecular alkylation reaction of D4-3-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 receptorsD4-3-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
