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...

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Authors: Comin, Maria Julieta; Rodriguez, Juan Bautista; Russ, Pam; Marquez, Victor E.
Format: Article
Status:Published version
Publication date:2003
Country:Argentina
Institution:Consejo Nacional de Investigaciones Científicas y Técnicas
Repository:CONICET Digital (CONICET)
Language:English
OAI Identifier:oai:ri.conicet.gov.ar:11336/85361
Online Access:http://hdl.handle.net/11336/85361
Access Level:Open access
Keyword: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
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author Comin, Maria Julieta
author2 Rodriguez, Juan Bautista
Russ, Pam
Marquez, Victor E.
author2_role author
author
author
author_browse Comin, Maria Julieta
Marquez, Victor E.
Rodriguez, Juan Bautista
Russ, Pam
author_facet Comin, Maria Julieta
Rodriguez, Juan Bautista
Russ, Pam
Marquez, Victor E.
author_role author
collection CONICET Digital (CONICET)
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.
eu_rights_str_mv openAccess
format article
id AR_7e69e2441cd8aed4c39d64dcc528cdc4
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
institution Consejo Nacional de Investigaciones Científicas y Técnicas
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
language eng
network_acronym_str AR
network_name_str Argentina
oai_identifier_str oai:ri.conicet.gov.ar:11336/85361
publishDate 2003
publishDateSort 2003
publisher Pergamon-Elsevier Science Ltd
publisherStr Pergamon-Elsevier Science Ltd
reponame_str CONICET Digital (CONICET)
spelling Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system Comin, Maria Julieta Rodriguez, Juan Bautista Russ, Pam Marquez, Victor E. 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 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. 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; Argentina Fil: 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; Argentina Fil: Russ, Pam. National Cancer Institute at Frederick; Estados Unidos Fil: Marquez, Victor E.. National Cancer Institute at Frederick; Estados Unidos Pergamon-Elsevier Science Ltd 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
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
status_str publishedVersion
title 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_short 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
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
topic_facet 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
url http://hdl.handle.net/11336/85361

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