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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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

id	todo:paper_14770520_v5_n15_p2453_DiChenna
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spelling	todo:paper_14770520_v5_n15_p2453_DiChenna2023-10-03T16:19:06Z Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones Di Chenna, P.H. Veleiro, A.S. Sonego, J.M. Ceballos, N.R. Garland, M.T. Baggio, R.F. Burton, G. Alkylation Derivatives Hormones Synthesis (chemical) Mineralocorticoid receptors Uterus progesterone receptors Organic compounds Rattus 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. Fil:Di Chenna, P.H. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Veleiro, A.S. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Sonego, J.M. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ceballos, N.R. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Burton, G. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. JOUR info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/2.5/ar http://hdl.handle.net/20.500.12110/paper_14770520_v5_n15_p2453_DiChenna
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Alkylation Derivatives Hormones Synthesis (chemical) Mineralocorticoid receptors Uterus progesterone receptors Organic compounds Rattus
spellingShingle	Alkylation Derivatives Hormones Synthesis (chemical) Mineralocorticoid receptors Uterus progesterone receptors Organic compounds Rattus Di Chenna, P.H. Veleiro, A.S. Sonego, J.M. Ceballos, N.R. Garland, M.T. Baggio, R.F. Burton, G. Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones
topic_facet	Alkylation Derivatives Hormones Synthesis (chemical) Mineralocorticoid receptors Uterus progesterone receptors Organic compounds Rattus
description	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.
format	JOUR
author	Di Chenna, P.H. Veleiro, A.S. Sonego, J.M. Ceballos, N.R. Garland, M.T. Baggio, R.F. Burton, G.
author_facet	Di Chenna, P.H. Veleiro, A.S. Sonego, J.M. Ceballos, N.R. Garland, M.T. Baggio, R.F. Burton, G.
author_sort	Di Chenna, P.H.
title	Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones
title_short	Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones
title_full	Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones
title_fullStr	Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones
title_full_unstemmed	Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones
title_sort	synthesis of 6,19-cyclopregnanes. constrained analogues of steroid hormones
url	http://hdl.handle.net/20.500.12110/paper_14770520_v5_n15_p2453_DiChenna
work_keys_str_mv	AT dichennaph synthesisof619cyclopregnanesconstrainedanaloguesofsteroidhormones AT veleiroas synthesisof619cyclopregnanesconstrainedanaloguesofsteroidhormones AT sonegojm synthesisof619cyclopregnanesconstrainedanaloguesofsteroidhormones AT ceballosnr synthesisof619cyclopregnanesconstrainedanaloguesofsteroidhormones AT garlandmt synthesisof619cyclopregnanesconstrainedanaloguesofsteroidhormones AT baggiorf synthesisof619cyclopregnanesconstrainedanaloguesofsteroidhormones AT burtong synthesisof619cyclopregnanesconstrainedanaloguesofsteroidhormones
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Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones

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