Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane

Autores
Garrido Santos, Gustavo A.; Murray, Ana Paula; Pujol, Carlos Alberto; Damonte, Elsa Beatriz; Maier, Marta Silvia
Año de publicación
2003
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Five new steroid sulfates, sodium 2β,3α-dihydroxy-5α-cholestane 3-sulfate (6), sodium 2β,3α-dihydroxy-5α-cholestane 2-sulfate (7), disodium 2β,3α-dihydroxy-5α-cholestane disulfate (8), sodium 3α-acetoxy-2β-hydroxy-5α-cholestane 2-sulfate (12), and sodium 2β-acetoxy-3α-hydroxy-5α-cholestane 3-sulfate (13), have been synthesized starting from 3β-hydroxy-5α-cholestane (1). The synthetic steroids were completely characterized by one-dimensional and two-dimensional NMR and FABMS spectra. Sulfation was performed using triethylamine-sulfur trioxide complex in dimethylformamide as the sulfating agent. The sulfated steroids were comparatively evaluated for their inhibitory effect on the replication of herpes simplex virus type 2 (HSV-2). Compounds 7 and 8 were the most effective in their inhibitory action against HSV-2. The disulfated steroid 8 also proved to be active against DEN-2 and JV.
Fil: Garrido Santos, Gustavo A.. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Murray, Ana Paula. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Pujol, Carlos Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina
Fil: Damonte, Elsa Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina
Fil: Maier, Marta Silvia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Materia
ANTIVIRAL ACTIVITY
SULFATED STEROIDS
SYNTHESIS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/85238
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/85238
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestaneGarrido Santos, Gustavo A.Murray, Ana PaulaPujol, Carlos AlbertoDamonte, Elsa BeatrizMaier, Marta SilviaANTIVIRAL ACTIVITYSULFATED STEROIDSSYNTHESIShttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Five new steroid sulfates, sodium 2β,3α-dihydroxy-5α-cholestane 3-sulfate (6), sodium 2β,3α-dihydroxy-5α-cholestane 2-sulfate (7), disodium 2β,3α-dihydroxy-5α-cholestane disulfate (8), sodium 3α-acetoxy-2β-hydroxy-5α-cholestane 2-sulfate (12), and sodium 2β-acetoxy-3α-hydroxy-5α-cholestane 3-sulfate (13), have been synthesized starting from 3β-hydroxy-5α-cholestane (1). The synthetic steroids were completely characterized by one-dimensional and two-dimensional NMR and FABMS spectra. Sulfation was performed using triethylamine-sulfur trioxide complex in dimethylformamide as the sulfating agent. The sulfated steroids were comparatively evaluated for their inhibitory effect on the replication of herpes simplex virus type 2 (HSV-2). Compounds 7 and 8 were the most effective in their inhibitory action against HSV-2. The disulfated steroid 8 also proved to be active against DEN-2 and JV.Fil: Garrido Santos, Gustavo A.. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Murray, Ana Paula. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Universidad Nacional del Sur. Departamento de Química; ArgentinaFil: Pujol, Carlos Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; ArgentinaFil: Damonte, Elsa Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; ArgentinaFil: Maier, Marta Silvia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaElsevier Science Inc2003-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/85238Garrido Santos, Gustavo A.; Murray, Ana Paula; Pujol, Carlos Alberto; Damonte, Elsa Beatriz; Maier, Marta Silvia; Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane; Elsevier Science Inc; Steroids; 68; 2; 2-2003; 125-1320039-128XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0039128X02001666info:eu-repo/semantics/altIdentifier/doi/10.1016/S0039-128X(02)00166-6info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-11-12T10:00:41Zoai:ri.conicet.gov.ar:11336/85238instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-11-12 10:00:42.289CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane
title Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane
spellingShingle Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane
Garrido Santos, Gustavo A.
ANTIVIRAL ACTIVITY
SULFATED STEROIDS
SYNTHESIS
title_short Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane
title_full Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane
title_fullStr Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane
title_full_unstemmed Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane
title_sort Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane
dc.creator.none.fl_str_mv Garrido Santos, Gustavo A.
Murray, Ana Paula
Pujol, Carlos Alberto
Damonte, Elsa Beatriz
Maier, Marta Silvia
author Garrido Santos, Gustavo A.
author_facet Garrido Santos, Gustavo A.
Murray, Ana Paula
Pujol, Carlos Alberto
Damonte, Elsa Beatriz
Maier, Marta Silvia
author_role author
author2 Murray, Ana Paula
Pujol, Carlos Alberto
Damonte, Elsa Beatriz
Maier, Marta Silvia
author2_role author
author
author
author
dc.subject.none.fl_str_mv ANTIVIRAL ACTIVITY
SULFATED STEROIDS
SYNTHESIS
topic ANTIVIRAL ACTIVITY
SULFATED STEROIDS
SYNTHESIS
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Five new steroid sulfates, sodium 2β,3α-dihydroxy-5α-cholestane 3-sulfate (6), sodium 2β,3α-dihydroxy-5α-cholestane 2-sulfate (7), disodium 2β,3α-dihydroxy-5α-cholestane disulfate (8), sodium 3α-acetoxy-2β-hydroxy-5α-cholestane 2-sulfate (12), and sodium 2β-acetoxy-3α-hydroxy-5α-cholestane 3-sulfate (13), have been synthesized starting from 3β-hydroxy-5α-cholestane (1). The synthetic steroids were completely characterized by one-dimensional and two-dimensional NMR and FABMS spectra. Sulfation was performed using triethylamine-sulfur trioxide complex in dimethylformamide as the sulfating agent. The sulfated steroids were comparatively evaluated for their inhibitory effect on the replication of herpes simplex virus type 2 (HSV-2). Compounds 7 and 8 were the most effective in their inhibitory action against HSV-2. The disulfated steroid 8 also proved to be active against DEN-2 and JV.
Fil: Garrido Santos, Gustavo A.. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Murray, Ana Paula. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Universidad Nacional del Sur. Departamento de Química; Argentina
Fil: Pujol, Carlos Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina
Fil: Damonte, Elsa Beatriz. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Biológica. Laboratorio de Virología; Argentina
Fil: Maier, Marta Silvia. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
description Five new steroid sulfates, sodium 2β,3α-dihydroxy-5α-cholestane 3-sulfate (6), sodium 2β,3α-dihydroxy-5α-cholestane 2-sulfate (7), disodium 2β,3α-dihydroxy-5α-cholestane disulfate (8), sodium 3α-acetoxy-2β-hydroxy-5α-cholestane 2-sulfate (12), and sodium 2β-acetoxy-3α-hydroxy-5α-cholestane 3-sulfate (13), have been synthesized starting from 3β-hydroxy-5α-cholestane (1). The synthetic steroids were completely characterized by one-dimensional and two-dimensional NMR and FABMS spectra. Sulfation was performed using triethylamine-sulfur trioxide complex in dimethylformamide as the sulfating agent. The sulfated steroids were comparatively evaluated for their inhibitory effect on the replication of herpes simplex virus type 2 (HSV-2). Compounds 7 and 8 were the most effective in their inhibitory action against HSV-2. The disulfated steroid 8 also proved to be active against DEN-2 and JV.
publishDate 2003
dc.date.none.fl_str_mv 2003-02
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/85238
Garrido Santos, Gustavo A.; Murray, Ana Paula; Pujol, Carlos Alberto; Damonte, Elsa Beatriz; Maier, Marta Silvia; Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane; Elsevier Science Inc; Steroids; 68; 2; 2-2003; 125-132
0039-128X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/85238
identifier_str_mv Garrido Santos, Gustavo A.; Murray, Ana Paula; Pujol, Carlos Alberto; Damonte, Elsa Beatriz; Maier, Marta Silvia; Synthesis and antiviral activity of sulfated and acetylated derivatives of 2β,3α-dihydroxy-5α-cholestane; Elsevier Science Inc; Steroids; 68; 2; 2-2003; 125-132
0039-128X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0039128X02001666
info:eu-repo/semantics/altIdentifier/doi/10.1016/S0039-128X(02)00166-6
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science Inc
publisher.none.fl_str_mv Elsevier Science Inc
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
_version_ 1848598492806643712
score 12.976206

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