Collect. Czech. Chem. Commun. 2006, 71, 15-34

Synthesis of Aminopropyl Phosphonate Nucleosides with Purine and Pyrimidine Bases

Ding Zhou, Irene M. Lagoja, Arthur Van Aerschot and Piet Herdewijn*

Laboratory of Medicinal Chemistry, Rega Institute, Minderbroedersstraat 10, B-3000 Leuven, Belgium


The synthesis and antiviral evaluation of new acyclic phosphonate nucleosides related to HPMPC (Cidofovir) has been described. These aminopropyl phosphonate nucleosides 1-3 have an amino function within either the acyclic chain (series 2 and 3) or as substituent (series 1). Both purine and pyrimidine nucleotide analogues have been synthesized. In contrast to HPMPC the oxygen analogue of 2c, only a weak antiherpes virus activity could be demonstrated for 2b and 2c.

Keywords: Acyclic nucleoside phosphonates; Acyclic nucleotide analogues; Aminopropyl phosphonic acids; Antiviral activity; Mitsunobu reaction.

References: 17 live references.