Two new families of N,O-nucleoside analogues containing the anthracene moiety introduced through the nitrosocarbonyl ene reaction with allylic alcohols were prepared. The core structure is an isoxazolidine heterocycle that introduces either atom either a phenyl ring or dimethyl moiety at the C3 carbon. Different heterobases were inserted at the position 5 of the heterocyclic ring. One of the synthesized compounds demonstrated a good capacity to induce cell death and an appreciable nuclear fragmentation was evidenced in treated cells.
Keywords: N,O-nucleosides; apoptosis; ene reactions; isoxazolidines; structure–activity relationship.
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.