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

DI CHENNA PABLO H.; VELEIRO, ADRIANA S.; SONEGO, JUAN S.; CEBALLOS, NORA; GARLAND, M. TERESA; BAGGIO, RICARDO; BURTON, GERARDO

Organic & Biomolecular Chemistry

RSC Publishing

Lugar: Cambridge; Año: 2007 vol. 5 p. 2453 - 2457

1477-0520

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 receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. 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. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. 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. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. 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. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. compound being more active. Both compounds did not compete with [3H]-aldosterone for kidney mineralocorticoid receptors nor with [3H]-R5020 for uterus progesterone receptors. mineralocorticoid receptors nor with [3