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

  1. Author:
    Comin, M. J.
    Rodriguez, J. B.
    Russ, P.
    Marquez, V. E.

  2. Author Address

    Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, Pabellon 2,Ciudad Univ, RA-1428 Buenos Aires, DF, Argentina Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, RA-1428 Buenos Aires, DF, Argentina NCI, Med Chem Lab, Canc Res Ctr, Frederick, MD 21702 USA Rodriguez JB Univ Buenos Aires, Fac Ciencias Exactas & Nat, Dept Quim Organ, Pabellon 2,Ciudad Univ, RA-1428 Buenos Aires, DF, Argentina
    1. Year: 2003
  2. Journal: Tetrahedron
    1. 59
    2. 3
    3. Pages: 295-301
  4. Type of Article: Article
  1. Abstract:

    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. (C) 2003 Elsevier Science Ltd. All rights reserved.

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