Norbornane-based nucleoside and nucleotide analogues locked in North conformation.

  title={Norbornane-based nucleoside and nucleotide analogues locked in North conformation.},
  author={Milan Dejmek and Michal {\vS}{\'a}la and Hubert Hřebabeck{\'y} and Martin Dra{\vc}{\'i}nsk{\'y} and Eli{\vs}ka Proch{\'a}zkov{\'a} and Dominika Chalupsk{\'a} and Martin Kl{\'i}ma and Pavla Pla{\vc}kov{\'a} and Miroslav H{\'a}jek and Graciella Andrei and Lieve M J Naesens and Pieter Leyssen and Johan Neyts and Jan Balzarini and Evzen Boura and Radim Nencka},
  journal={Bioorganic & medicinal chemistry},
  volume={23 1},
We report on the synthesis of novel conformationally locked nucleoside and nucleotide derivatives, which are structurally closely related to clinically used antivirals such as didanosine and abacavir. As a suitable conformationally rigid substitute of the sugar/pseudosugar ring allowing a permanent stabilization of the nucleoside in North conformation we employed bicyclo[2.2.1]heptane (norbornane) substituted in the bridgehead position with a hydroxymethyl group and in the C-3 position with a… CONTINUE READING