Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system

The rigid 6-oxobicyclo[3.1.0]hexane scaffold, characteristic of the natural antibiotic neplanocin C (3), was used to build prototypes of conformationally locked deoxynucleosides in the North hemisphere of the pseudorotational cycle. The purine analogues 6 and 7 are conformationally equivalent to car...

Descripción completa

Detalles Bibliográficos
Autores: Comin, Maria Julieta, Rodriguez, Juan Bautista, Russ, Pam, Marquez, Victor E.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2003
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/85361
Acceso en línea:http://hdl.handle.net/11336/85361
Access Level:acceso abierto
Palabra clave:2′-DEOXYNEPLANOCIN C
6-OXOBICYCLO[3.1.0]HEXANE
ANTIVIRAL ACTIVITY, EBV
CARBOCYCLIC NUCLEOSIDES
CONFORMATIONALLY LOCKED NUCLEOSIDES
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
id AR_7e69e2441cd8aed4c39d64dcc528cdc4
oai_identifier_str oai:ri.conicet.gov.ar:11336/85361
network_acronym_str AR
network_name_str Argentina
repository_id_str
spelling Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane systemComin, Maria JulietaRodriguez, Juan BautistaRuss, PamMarquez, Victor E.2′-DEOXYNEPLANOCIN C6-OXOBICYCLO[3.1.0]HEXANEANTIVIRAL ACTIVITY, EBVCARBOCYCLIC NUCLEOSIDESCONFORMATIONALLY LOCKED NUCLEOSIDEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The rigid 6-oxobicyclo[3.1.0]hexane scaffold, characteristic of the natural antibiotic neplanocin C (3), was used to build prototypes of conformationally locked deoxynucleosides in the North hemisphere of the pseudorotational cycle. The purine analogues 6 and 7 are conformationally equivalent to carbocyclic nucleosides built with the bicyclo[3.1.0]hexane template. The pyrimidine nucleosides were unstable and underwent a facile intramolecular epoxide ring-opening reaction leading to heterocycle 22. Only the deoxyguanosine analogue 7 showed antiviral activity against EBV.Fil: Comin, Maria Julieta. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaFil: Rodriguez, Juan Bautista. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaFil: Russ, Pam. National Cancer Institute at Frederick; Estados UnidosFil: Marquez, Victor E.. National Cancer Institute at Frederick; Estados UnidosPergamon-Elsevier Science Ltd2003-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/85361Comin, Maria Julieta; Rodriguez, Juan Bautista; Russ, Pam; Marquez, Victor E.; Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system; Pergamon-Elsevier Science Ltd; Tetrahedron; 59; 3; 1-2003; 295-3010040-4020CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/S0040-4020(02)01528-4info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0040402002015284info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T13:35:21Zoai:ri.conicet.gov.ar:11336/85361instacron: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:34982024-05-08 13:35:21.299CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
title Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
spellingShingle Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
Comin, Maria Julieta
2′-DEOXYNEPLANOCIN C
6-OXOBICYCLO[3.1.0]HEXANE
ANTIVIRAL ACTIVITY, EBV
CARBOCYCLIC NUCLEOSIDES
CONFORMATIONALLY LOCKED NUCLEOSIDES
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
title_short Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
title_full Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
title_fullStr Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
title_full_unstemmed Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
title_sort Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
dc.creator.none.fl_str_mv Comin, Maria Julieta
Rodriguez, Juan Bautista
Russ, Pam
Marquez, Victor E.
author Comin, Maria Julieta
author_facet Comin, Maria Julieta
Rodriguez, Juan Bautista
Russ, Pam
Marquez, Victor E.
author_role author
author2 Rodriguez, Juan Bautista
Russ, Pam
Marquez, Victor E.
author2_role author
author
author
dc.subject.none.fl_str_mv 2′-DEOXYNEPLANOCIN C
6-OXOBICYCLO[3.1.0]HEXANE
ANTIVIRAL ACTIVITY, EBV
CARBOCYCLIC NUCLEOSIDES
CONFORMATIONALLY LOCKED NUCLEOSIDES
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
topic 2′-DEOXYNEPLANOCIN C
6-OXOBICYCLO[3.1.0]HEXANE
ANTIVIRAL ACTIVITY, EBV
CARBOCYCLIC NUCLEOSIDES
CONFORMATIONALLY LOCKED NUCLEOSIDES
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
description The rigid 6-oxobicyclo[3.1.0]hexane scaffold, characteristic of the natural antibiotic neplanocin C (3), was used to build prototypes of conformationally locked deoxynucleosides in the North hemisphere of the pseudorotational cycle. The purine analogues 6 and 7 are conformationally equivalent to carbocyclic nucleosides built with the bicyclo[3.1.0]hexane template. The pyrimidine nucleosides were unstable and underwent a facile intramolecular epoxide ring-opening reaction leading to heterocycle 22. Only the deoxyguanosine analogue 7 showed antiviral activity against EBV.
publishDate 2003
dc.date.none.fl_str_mv 2003-01
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/11336/85361
Comin, Maria Julieta; Rodriguez, Juan Bautista; Russ, Pam; Marquez, Victor E.; Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system; Pergamon-Elsevier Science Ltd; Tetrahedron; 59; 3; 1-2003; 295-301
0040-4020
CONICET Digital
CONICET
url http://hdl.handle.net/11336/85361
identifier_str_mv Comin, Maria Julieta; Rodriguez, Juan Bautista; Russ, Pam; Marquez, Victor E.; Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system; Pergamon-Elsevier Science Ltd; Tetrahedron; 59; 3; 1-2003; 295-301
0040-4020
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/S0040-4020(02)01528-4
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0040402002015284
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
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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_ 1799194737786224640
score 15.81155

Similares en LA Referencia