Practical and efficient synthesis of pyrano[3,2-c]pyridone, pyrano[4,3-b]pyran and their hybrids with nucleoside as potential antiviral and antileishmanial agents

  • Bioorg Med Chem Lett. 2010 Feb 1;20(3):809-13. doi: 10.1016/j.bmcl.2009.12.102.
Xuesen Fan  1 ,  Dong Feng ,  Yingying Qu ,  Xinying Zhang ,  Jianji Wang ,  Philippe M Loiseau ,  Graciela Andrei ,  Robert Snoeck ,  Erik De Clercq
Affiliations
  • 1. School of Chemistry and Environmental Sciences, Henan Key Laboratory for Environmental Pollution Control, Henan Normal University, Xinxiang, Henan 453007, PR China.
PMID: 20064723 DOI: 10.1016/j.bmcl.2009.12.102
Abstract

A highly practical and efficient preparation of pyrano[3,2-c]pyridone and pyrano[4,3-b]pyran derivatives was developed via an ionic liquid mediated and promoted multi-component reaction of aldehyde (1), 4-hydroxy-pyridin-2(1H)-one or 4-hydroxy-2-pyranone (2), and malononitrile (3). As an application, a series of pyrimidine nucleoside-pyrano[3,2-c]pyridone or pyrano[4,3-b]pyran hybrids were efficiently obtained. These hybrid compounds were evaluated as potential Antiviral and antileishmanial agents and showed encouraging biological activities.