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Open AccessArticle

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

1
Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow 119991, Russia
2
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
*
Author to whom correspondence should be addressed.
The authors contributed equally.
Molecules 2017, 22(7), 1219; https://doi.org/10.3390/molecules22071219
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)
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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