Synthesis of Methylenecyclobutane Analogues of Nucleosides with Axial Chirality and Their Phosphoralaninates: A New Pronucleotide Effective against Epstein-Barr Virus
Free accessResearch articleFirst published online August, 2002
Synthesis of Methylenecyclobutane Analogues of Nucleosides with Axial Chirality and Their Phosphoralaninates: A New Pronucleotide Effective against Epstein-Barr Virus
Methylenecyclobutane analogues of 2′-deoxyadenosine, 2′-deoxyguanosine and 2′- deoxycytidine, and the corresponding phosphoralaninate pronucleotides comprising adenine and guanine bases, were synthesized as potential antiviral agents. Phosphoralaninate of adenine methylenecyclobutane was a potent inhibitor of replication of Epstein-Barr virus (EBV) in Daudi cell culture. Phosphoralaninate of guanine analogue was inactive but both pronucleotides were substrates for porcine liver esterase. Adenine methylenecyclobutane analogue was deaminated by adenosine deaminase.
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