Synthesis and anti-HIV activity of L-2'-fluoro-2',3'-unsaturated purine nucleosides

Article abstract of DOI:10.1016/S0040-4039(98)00841-7

The synthesis of 9-(2,3-dideoxy-2-fluoro-L-glycero-pent-2-eno- furanosyl)adenine and-hypoxanthine has been accomplished by direct condensation of silylated 6-chloropurine with key intermediates 8, which were prepared starting from 2,3-0-isopropylidene-L-glyceraldehyde. The synthesized nucleosides were evaluated against HIV-1 in vitro in primary human lymphocytes (PMB cells). It was found that β-L-Fd4A 12 exhibited moderately potent anti-HIV activity (EC₅₀ 1.5 μM).