Aryloxy phosphoramidate triesters as pro-tides.
We herein describe the development of aryloxy phosphoramidate triesters as an effective pro-tide motif for the intracellular delivery of charged bio-active antiviral nucleoside monophosphates. The review covers the discovery of such aryl phosphoramidates, their mechanism of action and structure-activity relationships. The application of this strategy to a range of antiviral nucleosides is highlighted.
Cahard
Dominique
D
UMR 6014 CNRS, Université de Rouen, Mont Saint Aignan cedex, France.
McGuigan
Christopher
C
Balzarini
Jan
J
D000577:Amides / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D015195:Drug Design; D004789:Enzyme Activation / Q000187:drug effects; D004952:Esters / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D006801:Humans; D015394:Molecular Structure; D009705:Nucleosides / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D010756:Phosphoric Acids / Q000737:chemistry*; D011355:Prodrugs / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D012680:Sensitivity and Specificity; D013329:Structure-Activity Relationship
D000577:Amides; D000596:Amino Acids; D000998:Antiviral Agents; D004952:Esters; D009705:Nucleosides; D010756:Phosphoric Acids; D011355:Prodrugs; C011067:phosphoramidic acid