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

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-O-isopropylidene-L-glyceraldehyde. The synthesized nucleosides were evaluated against HIV-1 in vitro in primary human lymphocytes (PMB cells). Ii was found that beta-L-Fd4A IZ exhibited moderately potent anti-HIV activity (EC50 1.5 mu M). (C) 1998 Elsevier Science Ltd. All rights reserved.