528841-70-5Relevant articles and documents
Synthesis of conformationally locked carbocyclic nucleosides built on an oxabicyclo[3.1.0]hexane system
Comin, María J.,Rodriguez, Juan B.,Russ, Pam,Marquez, Victor E.
, p. 295 - 301 (2007/10/03)
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.