ABSTRACT
Novel trans-2,2-dimethylcyclopropyl nucleosides were synthesized as potential antiviral agents. The key intermediate, 3, was synthesized via five steps from ethyl chrysanthemate and condensed with purine bases using the Mitsunobu reaction to give six cyclopropyl nucleosides. These synthesized nucleosides did not show any significant antiviral activity against HSV-1, HSV-2, EMCV, Cox B3, or VSV, at concentrations up to 100 microM.
Subject(s)
Antiviral Agents/chemical synthesis , Antiviral Agents/pharmacology , Nucleosides/chemical synthesis , Nucleosides/pharmacology , Encephalomyocarditis virus/drug effects , Encephalomyocarditis virus/growth & development , Herpesvirus 1, Human/drug effects , Herpesvirus 1, Human/growth & development , Herpesvirus 2, Human/drug effects , Herpesvirus 2, Human/growth & developmentABSTRACT
A series of novel exomethylene cyclopropyl nucleosides have been synthesized starting from Feist's acid. Classical nucleophilic substitution conditions (K2CO3, 18-crown-6) of the tosylate 2 as well as Mitsunobu reaction (DEAD, PPh3) of alcohol 1 with pyrimidine bases afforded a series of novel cyclopropyl nucleosides. Compound 4b displayed moderate anti-HBV activity without any cytotoxicity up to 100 microM.
