4'-alpha-C-Branched N,O-nucleosides: synthesis and biological properties

Ugo Chiacchio; Filippo Genovese; Daniela Iannazzo; Anna Piperno; Paolo Quadrelli; Corsaro Antonino; Roberto Romeo; Vincenza Valveri; Antonio Mastino

doi:10.1016/j.bmc.2004.04.041

4'-alpha-C-Branched N,O-nucleosides: synthesis and biological properties

Bioorg Med Chem. 2004 Jul 15;12(14):3903-9. doi: 10.1016/j.bmc.2004.04.041.

Authors

Ugo Chiacchio¹, Filippo Genovese, Daniela Iannazzo, Anna Piperno, Paolo Quadrelli, Corsaro Antonino, Roberto Romeo, Vincenza Valveri, Antonio Mastino

Affiliation

¹ Dipartimento Scienze Chimiche, Università di Catania, Viale Andrea Doria 6, 95125 Catania, Italy.

PMID: 15210157
DOI: 10.1016/j.bmc.2004.04.041

Abstract

The synthesis of 4'-alpha-C-branched N,O-nucleosides has been described, based on the 1,3-dipolar cycloaddition of nitrones with vinyl acetate followed by coupling with silylated nucleobases, The obtained compounds have been evaluated for their activity against HSV-1, HSV-2, HTLV-1. Cytotoxicity and apoptotic activity have been also investigated: compound 10c shows moderate apoptotic activity in Molt-3 cells.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antiviral Agents / chemical synthesis*
Antiviral Agents / pharmacology*
Apoptosis / drug effects
Cell Line
Herpesvirus 1, Human / drug effects
Herpesvirus 2, Human / drug effects
Human T-lymphotropic virus 1 / drug effects
Humans
Magnetic Resonance Spectroscopy
Nucleosides / chemical synthesis*
Nucleosides / pharmacology*
Spectrometry, Mass, Fast Atom Bombardment

Substances

Antiviral Agents
Nucleosides