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, Pablo Héctor, Veleiro, Adriana Silvia, Sonego, Juan Manuel, Ceballos, Nora Raquel, Burton, Gerardo
Publicado:	2007
Materias:	Alkylation Derivatives Hormones Synthesis (chemical) Mineralocorticoid receptors Uterus progesterone receptors Organic compounds Rattus
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v5_n15_p2453_DiChenna 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	paper:paper_14770520_v5_n15_p2453_DiChenna
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spelling	paper:paper_14770520_v5_n15_p2453_DiChenna2023-06-08T16:18:06Z Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones Di Chenna, Pablo Héctor Veleiro, Adriana Silvia Sonego, Juan Manuel Ceballos, Nora Raquel Burton, Gerardo 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. 2007 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v5_n15_p2453_DiChenna 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, Pablo Héctor Veleiro, Adriana Silvia Sonego, Juan Manuel Ceballos, Nora Raquel Burton, Gerardo 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.
author	Di Chenna, Pablo Héctor Veleiro, Adriana Silvia Sonego, Juan Manuel Ceballos, Nora Raquel Burton, Gerardo
author_facet	Di Chenna, Pablo Héctor Veleiro, Adriana Silvia Sonego, Juan Manuel Ceballos, Nora Raquel Burton, Gerardo
author_sort	Di Chenna, Pablo Héctor
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
publishDate	2007
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_14770520_v5_n15_p2453_DiChenna http://hdl.handle.net/20.500.12110/paper_14770520_v5_n15_p2453_DiChenna
work_keys_str_mv	AT dichennapablohector synthesisof619cyclopregnanesconstrainedanaloguesofsteroidhormones AT veleiroadrianasilvia synthesisof619cyclopregnanesconstrainedanaloguesofsteroidhormones AT sonegojuanmanuel synthesisof619cyclopregnanesconstrainedanaloguesofsteroidhormones AT ceballosnoraraquel synthesisof619cyclopregnanesconstrainedanaloguesofsteroidhormones AT burtongerardo synthesisof619cyclopregnanesconstrainedanaloguesofsteroidhormones
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Synthesis of 6,19-cyclopregnanes. Constrained analogues of steroid hormones

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