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Molecules 2017, 22(7), 1219;

Fluorination of Naturally Occurring N6-Benzyladenosine Remarkably Increased Its Antiviral Activity and Selectivity

Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow 119991, Russia
Laboratory for Virology and Chemotherapy, Department of Microbiology and Immunology, Rega Institute for Medical Research, KU Leuven-University of Leuven, Minderbroedersstraat 10, Leuven 3000, Belgium
The authors contributed equally.
Author to whom correspondence should be addressed.
Received: 27 June 2017 / Revised: 13 July 2017 / Accepted: 17 July 2017 / Published: 20 July 2017
(This article belongs to the Special Issue Nucleoside and Nucleotide Analogues)
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Recently, we demonstrated that the natural cytokinin nucleosides N6-isopentenyladenosine (iPR) and N6-benzyladenosine (BAPR) exert a potent and selective antiviral effect on the replication of human enterovirus 71. In order to further characterize the antiviral profile of this class of compounds, we generated a series of fluorinated derivatives of BAPR and evaluated their activity on the replication of human enterovirus 71 in a cytopathic effect (CPE) reduction assay. The monofluorination of the BAPR-phenyl group changed the selectivity index (SI) slightly because of the concomitant high cell toxicity. Interestingly, the incorporation of a second fluorine atom resulted in a dramatic improvement of selectivity. Moreover, N6-trifluoromethylbenzyladenosine derivatives (911) exhibited also a very interesting profile, with low cytotoxicity observed. In particular, the analogue N6-(3-trifluoromethylbenzyl)-adenosine (10) with a four-fold gain in potency as compared to BAPR and the best SI in the class represents a promising candidate for further development. View Full-Text
Keywords: fluorinated N6-benzyladenosines; synthesis and antiviral activity; SAR; enterovirus 71 fluorinated N6-benzyladenosines; synthesis and antiviral activity; SAR; enterovirus 71

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Oslovsky, V.E.; Drenichev, M.S.; Sun, L.; Kurochkin, N.N.; Kunetsky, V.E.; Mirabelli, C.; Neyts, J.; Leyssen, P.; Mikhailov, S.N. Fluorination of Naturally Occurring N6-Benzyladenosine Remarkably Increased Its Antiviral Activity and Selectivity. Molecules 2017, 22, 1219.

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