Learning from the lesson of anti-HHV hexitol nucleosides, compounds 1-4 are conceived as conformational preorganized nucleosides, exploiting the rigidity of the piperidinyl core to improve inhibition potency and selectivity. Access to nucleosides 1-4 has been devised starting from the well-known glucosidase inhibitor 1-deoxynojirimycin (DNJ), (3) efficiently prepared with a general and highly selective procedure by a de novo synthetic approach.
Synthesis and Biological Evaluation of Novel Piperidinyl Iminosugar-Based Nucleoside / DE FENZA, Maria; Esposito, Anna; Andrei, Graciela; Snoeck, Robert; Guaragna, Annalisa; D'Alonzo, Daniele. - (2017). (Intervento presentato al convegno XXVI Congresso Nazionale della Società Chimica Italiana tenutosi a Paestum (SA), Italia nel 10-14 settembre 2017).