A new adenine derivative is prepared through the chemistry of nitrosocarbonyl intermediates. The synthesis relies upon the functionalization of adenine by inserting an ester moiety, to be transformed into the corresponding hydroxamic acid. The oxidation conducted in situ in the presence of cyclopentadiene afforded the hetero Diels-Alder cycloadduct, furtherly elaborated to give the target nucleoside analogue. This single product displayed a selective high activity against HPV. The EC50 and EC90 values are remarkably lower than the values collected for Cidofovir used as control drug. The EC50 is 39 times lower while the CC50 value is 97.11 mM.
Pericyclic Reactions for Anti-HPV Antivirals: Unconventional Nucleoside Analogue Synthesis via Nitrosocarbonyl Chemistry
Al-saad, Dalya;Memeo, Misal Giuseppe;Quadrelli, Paolo
2017-01-01
Abstract
A new adenine derivative is prepared through the chemistry of nitrosocarbonyl intermediates. The synthesis relies upon the functionalization of adenine by inserting an ester moiety, to be transformed into the corresponding hydroxamic acid. The oxidation conducted in situ in the presence of cyclopentadiene afforded the hetero Diels-Alder cycloadduct, furtherly elaborated to give the target nucleoside analogue. This single product displayed a selective high activity against HPV. The EC50 and EC90 values are remarkably lower than the values collected for Cidofovir used as control drug. The EC50 is 39 times lower while the CC50 value is 97.11 mM.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
