2β-3, 4-Unsaturated sialic acid derivatives: Synthesis optimization, and biological evaluation as Newcastle disease virus hemagglutinin-neuraminidase inhibitors. Issue 14 (15th July 2020)

• Record Type: Journal Article
• Authors: La Rocca, Paolo; Rota, Paola; Piccoli, Marco; Cirillo, Federica; Ghiroldi, Andrea; Franco, Valentina; Allevi, Pietro; Anastasia, Luigi
• Is Part Of: Bioorganic & medicinal chemistry. Volume 28:Issue 14(2020)
• Publication Date: 2020-07-15
• Subjects: Ferrier reaction -- Montmorillonite -- Newcastle disease virus -- Hemagglutinin-neuraminidase -- Sialidase inhibitor; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; Biochemistry -- Periodicals; Chemistry, Clinical -- Periodicals; Chemistry, Organic -- Periodicals; Chimie bio-organique -- Périodiques; Chimie pharmaceutique -- Périodiques; 615.19
• DOI: 10.1016/j.bmc.2020.115563
• Languages: English
• ISSNs: 0968-0896

Abstract

Graphical abstract: 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.