Convenient synthesis of nucleoside and isonucleoside analogues.

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...

Synthesis of Some New 1-[2-(alkylthio-1-benzyl-5-imidazolyl) carbonyl]-4-[3-(isopropylamino)-2-pyridyl] piperazines as Anti-HIV

A few analogues of atevirdine or 1-[(5-methoxyindol-2-yl) carbonyl]-4-[3- (ethylamino)-2-pyridyl] piperazine – an anti-HIV belonging to non-nucleoside reverse transcriptase inhibitors were synthesized and evaluated for anti-HIV activity. Replacement of indolyl moiety with 2-alkylthio-1-benzyl-5-imidazolyl substituent afforded 1-[2-(alkylthio-1-benzyl-5-imidazolyl) carbonyl]-4-[3-(isopropylamino...

Chemical Synthesis of Nucleoside Analogues Chemical Synthesis of Nucleoside Analogues

An efficient solid phase synthesis of 5'-phosphodiester and phosphoramidate monoester nucleoside analogues.

An easy and efficient strategy to obtain libraries of 5'-phosphodiester and 5'-phosphoramidate monoester nucleoside analogues in a highly pure form has been developed, starting from a new nucleoside based solid support. The nucleoside scaffold has been anchored through a 5'-phosphodiester linkage to Tentagel HL resin, functionalized with a 3-chloro-4-hydroxyphenylacetic linker. The solid phase ...

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...