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

P. La Rocca, P. Rota, M. Piccoli, F. Cirillo, A. Ghiroldi, V. Franco, P. Allevi, L. Anastasia

Research output: Contribution to journalArticlepeer-review

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. © 2020 Elsevier Ltd
Original languageEnglish
JournalBioorg. Med. Chem.
Volume28
Issue number14
DOIs
Publication statusPublished - 2020

Keywords

  • Ferrier reaction
  • Hemagglutinin-neuraminidase
  • Montmorillonite
  • Newcastle disease virus
  • Sialidase inhibitor
  • 2beta 3,4 unsaturated sialic acid derivative
  • sialidase inhibitor
  • unclassified drug
  • Article
  • carbon nuclear magnetic resonance
  • catalyst
  • chemical reaction
  • column chromatography
  • controlled study
  • deacetylation
  • drug conformation
  • drug potency
  • drug selectivity
  • drug synthesis
  • enzyme active site
  • human
  • IC50
  • molecular docking
  • proton nuclear magnetic resonance
  • reaction optimization
  • reaction temperature
  • stereoselectivity

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