Synthesis of new acadesine (AICA-riboside) analogues having acyclic D-ribityl or 4-hydroxybutyl chains in place of the ribose

Stefano D'Errico; Giorgia Oliviero; Nicola Borbone; Jussara Amato; Vincenzo Piccialli; Michela Varra; Luciano Mayol; Gennaro Piccialli

doi:10.3390/molecules18089420

Synthesis of new acadesine (AICA-riboside) analogues having acyclic D-ribityl or 4-hydroxybutyl chains in place of the ribose

Molecules. 2013 Aug 6;18(8):9420-31. doi: 10.3390/molecules18089420.

Authors

Stefano D'Errico¹, Giorgia Oliviero, Nicola Borbone, Jussara Amato, Vincenzo Piccialli, Michela Varra, Luciano Mayol, Gennaro Piccialli

Affiliation

¹ Dipartimento di Farmacia, Università degli Studi di Napoli Federico II, Via D. Montesano 49, Napoli 80131, Italy.

Abstract

The antiviral activity of certain acyclic nucleosides drew our attention to the fact that the replacement of the furanose ring by an alkyl group bearing hydroxyl(s) could be a useful structural modification to modulate the biological properties of those nucleosides. Herein, we report on the synthesis of some novel acadesine analogues, where the ribose moiety is mimicked by a D-ribityl or by a hydroxybutyl chain.

Publication types

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

MeSH terms

Aminoimidazole Carboxamide / analogs & derivatives*
Aminoimidazole Carboxamide / chemical synthesis
Aminoimidazole Carboxamide / pharmacology
Antiviral Agents / chemical synthesis*
Antiviral Agents / pharmacology
Humans
Nucleotides / chemistry
Ribonucleosides / chemical synthesis*
Ribonucleosides / pharmacology
Ribose / chemistry*
Structure-Activity Relationship*
Viruses / drug effects

Substances

Antiviral Agents
Nucleotides
Ribonucleosides
Aminoimidazole Carboxamide
acadesine
Ribose