2β-3,4-Unsaturated sialic acid derivatives: Synthesis optimization, and biological evaluation as Newcastle disease virus hemagglutinin-neuraminidase inhibitors

Paolo La Rocca, Paola Rota, Marco Piccoli, Federica Cirillo, Andrea Ghiroldi, Valentina Franco, Pietro Allevi, Luigi Anastasia

Research output: Contribution to journalArticle

Abstract

The optimization of the synthetic protocol to obtain the 3,4-unsaturated sialic acid derivatives, through the fine-tuning of both the Ferrier glycosylation conditions and the subsequent hydrolysis work-up, is herein reported. The accomplishment of the desired β-anomers and some selected α-ones, in pure form, led us to evaluate their specific inhibitory activity towards NDV-HN and human sialidase NEU3. Importantly, the resulting data allowed the identification, for the first time, of three active 3,4-unsaturated sialic acid analogs, showing IC50 values against NDV-HN in the micromolar range.

Original languageEnglish
Pages (from-to)115563
JournalBioorganic and Medicinal Chemistry
Volume28
Issue number14
DOIs
Publication statusPublished - Jul 15 2020

Fingerprint Dive into the research topics of '2β-3,4-Unsaturated sialic acid derivatives: Synthesis optimization, and biological evaluation as Newcastle disease virus hemagglutinin-neuraminidase inhibitors'. Together they form a unique fingerprint.

  • Cite this