[4'-Branched nucleosides. II. Synthesis of 4'-hydroxymethyl derivatives of 2',3'-anhydronucleosides of the ribo- and lyxo-series].
A general synthetic method for 4'-hydroxymethyl-2',3'-anhydronucleosides from 1,2-O-isopropylidene-4-hydroxymethyl-alpha-D-xylofuranose is described. The condensation of 1,2-di-O-acetyl-3-O-methanesulphonyl-4-benzoyloxymethyl-5-O- benzoyl-D-xylofuranose with trimethylsilyl derivatives of N6-benzoyladenine and N2-palmitoylguanine in the presence of stannic chloride resulted in the corresponding nucleosides. After their treatment with NH4OH-EtOH, corresponding 2',3'-riboanhydronucleosides were isolated. Condensation of 1,2-di-O-acetyl-3-O-benzoyl-4-benzoyloxymethyl-5-O-benzoyl-D-xy lofuranose with trimethylsilyl derivatives of purines followed by selective deacetylation led to the nucleosides with free 2'-OH group. Their 2'-O-mesylation and epoxidering closure resulted in the isolation of 2',3'-anhydrolyxonucleosides with 38-44% yields. All the compounds synthesized did not inhibit HIV-1 reproduction in human H9 and PBL cell cultures nor HSV-2 and HCMV reproduction in vero cells up to 100 microM concentrations.
Surzhikov
S A
SA
D000998:Antiviral Agents / Q000494:pharmacology; D002478:Cells, Cultured; D003587:Cytomegalovirus / Q000187:drug effects / Q000502:physiology; D015497:HIV-1 / Q000187:drug effects / Q000502:physiology; D018258:Herpesvirus 2, Human / Q000187:drug effects / Q000502:physiology; D006801:Humans; D006900:Hydroxylation; D008745:Methylation; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D014779:Virus Replication / Q000187:drug effects
D000998:Antiviral Agents; D011684:Purine Nucleosides
4'-Razvetvlennye nukleozidy. II. Sintez 4'-gidroksimetil'nykh proizvodnykh purinovykh 2',3'-angidronukleozidov ribo- i likso-riada.