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...
| Authors: | ; ; ; |
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| 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 |
| Summary: | 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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