Synthesis of Novel 2′(β)-Methyl-5′-deoxyapiose Nucleoside Phosphonic Acid Analogues as Antiviral Agents

다국어 초록 (Multilingual Abstract)

Novel 2'(β)-methyl-5'-deoxyapiose purine phosphonic acid analogues were designed and synthesized from 2-propanone-1,3-diacetate. Condensation successfully proceeded from a glycosyl donor 9 under Vorbrüggen conditions. Condensationof aldehyde 14 with Wittig reagent [(diethoxyphosphinyl)methylidene] triphenylphosphorane gave the desired nucleosidephosphonate analogues 15. Ammonolysis and hydrolysis of phosphonates gave the nucleoside phosphonic acid analogue17 and 19. The synthesized nucleoside analogues were subjected to antiviral screening against HIV-1. The adenineanalogue 19 exhibited weak in vitro activities against HIV-1.

참고문헌 (Reference)

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16 "All geometries were optimized with the framework of the density functional theory (DFT), with Spartan modeling software. The B3LYP functional with 6-31G* basis set was employed"