Synthesis of O-Nicotinoyl-Substituted Depot Forms of Biologically Active N6-Benzyladenosine Analogs
Anastasia A Zenchenko1, Irina V Varizhuk1, Mikhail S Drenichev1
1Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia.
Abstract:
This unit describes an effective method for the preparation of N6-benzyl-2',3',5'-tri-O-nicotinoyl adenosine and N6-(3-fluorobenzyl)-2',3',5'-tri-O-nicotinoyl adenosine. These compounds are depot forms of biologically active N6-benzyladenosine (BAR) and its fluorinated analog N6-(3-fluorobenzyl)adenosine (FBAR), which had previously shown pronounced antiviral activity against human enterovirus EV-A71. BAR and FBAR bearing biodegradable O-nicotinoyl ester moieties were obtained by a three-step synthesis starting from inosine. An attractive feature of this strategy is the possibility of obtaining biodegradable depot forms of various biologically active ribonucleoside derivatives, particularly N6-substituted adenosine derivatives. © 2025 Wiley Periodicals LLC. Basic Protocol: Preparation of N6-benzyl-2',3',5'-tri-O-nicotinoyl adenosine (4a). Alternate Protocol: Preparation of N6-(3-fluorobenzyl)-2',3',5'-tri-O-nicotinoyl adenosine (4b).
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