Synthesis and potent anti-leukemic activity of novel 5'-deoxycarbocyclic C-nucleoside phosphonic acids

The first synthetic route to 5'-deoxycarbocyclic C-nucleoside [9-deazaadenosine, (pyrrolo[3,2-d]pyrimidine)] phosphonic acids from commercially available 1,4-dihydroxy-2-butene was described. The key C-C bond formation from cyclopentanone to base precursor was performed using Knoevenagel-type condensation. Synthesized C-nucleoside phosphonic acids were tested for anti-HIV activity as well as anti-leukemic activity. They showed moderate cytotoxicity derived anti-HIV activity and anti-leukemic activity.