Aryl nucleoside H-phosphonates. Part 15: Synthesis, properties and, anti-HIV activity of aryl nucleoside 5′-α-hydroxyphosphonates Original Research Article

Aryl nucleoside 5′-H-phosphonates 4 bearing AZT or 2′,3′-dideoxyuridine moieties were subjected to reaction with various aromatic aldehydes to produce nucleoside 5′-α-hydroxyphosphonate derivatives 2 as potential anti-HIV agents. Stability of the title compounds in cell culture media was investigated and three distinct decomposition pathways were identified. The anti-HIV activity of hydroxyphosphonates 2 correlates well with the type and extent of their chemical or enzymatic degradation in culture medium (RPMI 1640 containing 10% FBS), suggesting that aryl nucleoside 5′-hydroxyphosphonates 2 act as depot forms of the parent antiviral nucleosides.