A NEW CLASS OF ACYCLIC NUCLEOSIDE PHOSPHONATES: SYNTHESIS AND BIOLOGICAL ACTIVITY OF 9-{[(PHOSPHONOMETHYL)AZIRIDIN-1-YL]METHYL}GUANINE (PMAMG) AND ANALOGUES

ABSTRACT

A new class of acyclic nucleoside phosphonates PMAMG, PMAMA, PMAMC, and PMAMT (compounds 1, 2, 3 and4) have been synthesized and tested in vitro against a wide variety of viruses, fungi and bacteria. PMAMG (1) was synthesized by the alkylation reaction of acetylguanine with the phosphonate side-chain, diisopropyl {[2-(bromomethyl)aziridin-1-yl]methyl}phosphonate (9), followed by deesterification reaction in the presence of TMSBr. In similar way, PMAMA, PMAMC, and PMAMT were prepared.

ACKNOWLEDGMENTS

The authors wish to thank Dr Daniela Ghiani for editing the manuscript. This study was supported in part by grants of the Scientific Deanship Research of the Applied Science University and Istituto Superiore di Sanità-Progetto AIDS (N° 40A.0.55).