Synthesis of 6,19-sulfamidate bridged pregnanes

Conformationally restrained substituted pregnane-20-one derivatives were obtained by an intramolecular nitrene addition onto a C-5/C-6 double bond involving a tethered C-19 sulfamoyl moiety. The resulting aziridine underwent regioselective nucleophilic ring opening at C-5 at room temperature with cy...

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Autores principales:	Durán, Fernando Javier, Ghini, Alberto Antonio, Burton, Gerardo
Publicado:	2005
Materias:	Addition reactions Conformations Ring opening polymerization Stereochemistry Substitution reactions Sulfur compounds 6,9-sulfamidate bridged pregnanes Nitrene Nucleophilic ring opening Regioselectivity Aromatic compounds 4 aminobutyric acid A receptor acetic acid aziridine derivative cyanide fluoride neurosteroid pregnane derivative sulfanilamide anticonvulsant activity article chemical reaction conformational transition derivatization molecular interaction reaction analysis ring opening solubility synthesis Bridged Compounds Molecular Structure Pregnanes Sulfonic Acids
Acceso en línea:	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v70_n21_p8613_Duran http://hdl.handle.net/20.500.12110/paper_00223263_v70_n21_p8613_Duran
Aporte de:	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) de Universidad de Buenos Aires

id	paper:paper_00223263_v70_n21_p8613_Duran
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spelling	paper:paper_00223263_v70_n21_p8613_Duran2023-06-08T14:49:34Z Synthesis of 6,19-sulfamidate bridged pregnanes Durán, Fernando Javier Ghini, Alberto Antonio Burton, Gerardo Addition reactions Conformations Ring opening polymerization Stereochemistry Substitution reactions Sulfur compounds 6,9-sulfamidate bridged pregnanes Nitrene Nucleophilic ring opening Regioselectivity Aromatic compounds 4 aminobutyric acid A receptor acetic acid aziridine derivative cyanide fluoride neurosteroid pregnane derivative sulfanilamide anticonvulsant activity article chemical reaction conformational transition derivatization molecular interaction reaction analysis ring opening solubility synthesis Bridged Compounds Molecular Structure Pregnanes Sulfonic Acids Conformationally restrained substituted pregnane-20-one derivatives were obtained by an intramolecular nitrene addition onto a C-5/C-6 double bond involving a tethered C-19 sulfamoyl moiety. The resulting aziridine underwent regioselective nucleophilic ring opening at C-5 at room temperature with cyanide, fluoride, and acetate. In the isolated case of acetate, a reversal of regioselectivity was observed at higher temperatures, a result attributed to a rearrangement process involving aziridine ring opening at the C-5 position and subsequent migration of the acetyl meiety to C-6. © 2005 American Chemical Society. Fil:Duran, F.J. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales; Argentina. Fil:Ghini, A.A. 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. 2005 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v70_n21_p8613_Duran http://hdl.handle.net/20.500.12110/paper_00223263_v70_n21_p8613_Duran
institution	Universidad de Buenos Aires
institution_str	I-28
repository_str	R-134
collection	Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA)
topic	Addition reactions Conformations Ring opening polymerization Stereochemistry Substitution reactions Sulfur compounds 6,9-sulfamidate bridged pregnanes Nitrene Nucleophilic ring opening Regioselectivity Aromatic compounds 4 aminobutyric acid A receptor acetic acid aziridine derivative cyanide fluoride neurosteroid pregnane derivative sulfanilamide anticonvulsant activity article chemical reaction conformational transition derivatization molecular interaction reaction analysis ring opening solubility synthesis Bridged Compounds Molecular Structure Pregnanes Sulfonic Acids
spellingShingle	Addition reactions Conformations Ring opening polymerization Stereochemistry Substitution reactions Sulfur compounds 6,9-sulfamidate bridged pregnanes Nitrene Nucleophilic ring opening Regioselectivity Aromatic compounds 4 aminobutyric acid A receptor acetic acid aziridine derivative cyanide fluoride neurosteroid pregnane derivative sulfanilamide anticonvulsant activity article chemical reaction conformational transition derivatization molecular interaction reaction analysis ring opening solubility synthesis Bridged Compounds Molecular Structure Pregnanes Sulfonic Acids Durán, Fernando Javier Ghini, Alberto Antonio Burton, Gerardo Synthesis of 6,19-sulfamidate bridged pregnanes
topic_facet	Addition reactions Conformations Ring opening polymerization Stereochemistry Substitution reactions Sulfur compounds 6,9-sulfamidate bridged pregnanes Nitrene Nucleophilic ring opening Regioselectivity Aromatic compounds 4 aminobutyric acid A receptor acetic acid aziridine derivative cyanide fluoride neurosteroid pregnane derivative sulfanilamide anticonvulsant activity article chemical reaction conformational transition derivatization molecular interaction reaction analysis ring opening solubility synthesis Bridged Compounds Molecular Structure Pregnanes Sulfonic Acids
description	Conformationally restrained substituted pregnane-20-one derivatives were obtained by an intramolecular nitrene addition onto a C-5/C-6 double bond involving a tethered C-19 sulfamoyl moiety. The resulting aziridine underwent regioselective nucleophilic ring opening at C-5 at room temperature with cyanide, fluoride, and acetate. In the isolated case of acetate, a reversal of regioselectivity was observed at higher temperatures, a result attributed to a rearrangement process involving aziridine ring opening at the C-5 position and subsequent migration of the acetyl meiety to C-6. © 2005 American Chemical Society.
author	Durán, Fernando Javier Ghini, Alberto Antonio Burton, Gerardo
author_facet	Durán, Fernando Javier Ghini, Alberto Antonio Burton, Gerardo
author_sort	Durán, Fernando Javier
title	Synthesis of 6,19-sulfamidate bridged pregnanes
title_short	Synthesis of 6,19-sulfamidate bridged pregnanes
title_full	Synthesis of 6,19-sulfamidate bridged pregnanes
title_fullStr	Synthesis of 6,19-sulfamidate bridged pregnanes
title_full_unstemmed	Synthesis of 6,19-sulfamidate bridged pregnanes
title_sort	synthesis of 6,19-sulfamidate bridged pregnanes
publishDate	2005
url	https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00223263_v70_n21_p8613_Duran http://hdl.handle.net/20.500.12110/paper_00223263_v70_n21_p8613_Duran
work_keys_str_mv	AT duranfernandojavier synthesisof619sulfamidatebridgedpregnanes AT ghinialbertoantonio synthesisof619sulfamidatebridgedpregnanes AT burtongerardo synthesisof619sulfamidatebridgedpregnanes
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Synthesis of 6,19-sulfamidate bridged pregnanes

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