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...
| Autores: | , , , |
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| 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 |
| Sumario: | 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. |
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