Synthesis of 2',3'-Cyclohexene Bicyclic Nucleoside Analogues as Antiviral Compounds

Photochemical synthesis of nucleoside analogues from cyclobutanones: bicyclic and isonucleosides.

The preparation of two nucleoside analogues are reported. Both syntheses involve a key photochemical ring-expansion of cyclobutanones to an oxacarbene and its subsequent scavenging by 6-chloropurine. The synthesis of a bicyclic (locked) purine starts from a oxabicycloheptanone with a hydroxymethyl pendant. The preparation of an isonucleoside uses a cyclobutanone with an alpha-substituted 6-chlo...

Chemical Synthesis of Nucleoside Analogues Chemical Synthesis of Nucleoside Analogues

Antiviral activity of nucleoside analogues against norovirus.

BACKGROUND Norovirus (NoV) is the leading cause of epidemic gastroenteritis worldwide. The lack of a cell culture has significantly hampered the development of effective therapies against human NoV. Clinically approved nucleoside and non-nucleoside analogues have been used successfully against RNA viruses. METHODS In this study, we evaluated the efficacy of four nucleoside analogues (2'-C-MeC...

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

Novel 2'(β)-methyl-5'-deoxyapiose purine phosphonic acid analogues were designed and synthesized from 2-propanone1,3-diacetate. Condensation successfully proceeded from a glycosyl donor 9 under Vorbrüggen conditions. Condensation of aldehyde 14 with Wittig reagent [(diethoxyphosphinyl)methylidene] triphenylphosphorane gave the desired nucleoside phosphonate analogues 15. Ammonolysis and hydroly...

Combinatorial synthesis of galactosyl-1,3,5-triazines as novel nucleoside analogues.

Herein we report a parallel solid-phase synthesis of 1,3,5-triazine based nucleoside analogues by a three-step substitution, starting from 2,4,6-trichloro-1,3,5-triazine. A library of 80 galactosyl-1,3,5-triazine compounds was prepared in high purity without extensive reaction conditions or tedious purification, suggesting the generality of this method.