Pericyclic Reactions for Anti‐HPV Antivirals: Unconventional Nucleoside Analogue Synthesis via Nitrosocarbonyl Chemistry

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 μM.

Synthesis and Biological Evaluation of Glycosides and Acyclic Nucleosides Derived 2‐Oxonicotinonitriles

“…IR spectrum of 27 showed ν C═S = 1213 cm À1 , and its 13 C NMR spectrum of 27 showed the signal for (C2) at 176.44 ppm. Energies of 7 and 27 tautomers were calculated via density functional theory at B3LYP/631G* level of theory [49]. Energies listed in Table 1 show the predominance of the amide tautomer (A1) for 7 and thioamide tautomer (A3) for 27 over the corresponding 2-hydroxypyridine (A2) and 2mercaptopyridine (A4) tautomers, respectively ( Fig.…”

Synthesis and antiviral activity of diverse heterocyclic scaffolds

“…Al‐Saad et al (2017) have prepared a new adenine derivative 381 through the formation of nitrosocarbonyl intermediate 379b (Scheme 67). Synthesis of nucleoside analogues involved the functionalization of adenine by ester moiety which was transformed to hydroxamic acid and in the presence of cyclopentadiene followed Diels‐Alder cycloaddition reaction.…”