Efficient one-pot, three-component procedure to prepare new α-aminophosphonate and phosphonic acid acyclic nucleosides

Abstract

An efficient one-pot three-component Kabachnik–Fields reaction of aldehydes (acyclic nucleosides), amines (or amino acid), and triethyl phosphite proceeded for the synthesis of aminophosphonates using natural phosphate coated with iodine (I₂@NP) as a catalyst. The novel α-aminophosphonate and phosphonic acid acyclic nucleosides were tested for their anti-HCV and anti-HIV activities. The molecular docking showed that the non-activity of these compounds could be due to the absence of hydrophobic pharmacophores.

Keywords:

• Acyclic nucleosides
• α-aminophosphonates
• Kabachnik–Fields reaction
• catalysis
• natural phosphate

Acknowledgments

The authors would like to thank Professor J. Balzarini, Professor J. Neyts (Rega Institute for Medical Research, Katholieke University Leuven, Leuven, Belgium), and Professor S. Sebti (Faculty of Science BenM’sik, University Hassan II, Casablanca, Morocco) for their scientific contribution and help on the realization of this work. Also, they would like to acknowledge the technical staff of the CAC (Centre of Analysis and Characterization), Cadi Ayyad University, Marrakech for running the spectroscopic analysis.

Additional information

Funding

This project was supported by the comité mixte inter-universitaire Franco-Marocain programme (A.I. N° Ma/06/143) and by Centre National de Recherche Scientifique et Technique project RS/2011/01 (Rabat, Morocco).