Issue 9, 2017

Sugar modified pyrimido[4,5-b]indole nucleosides: synthesis and antiviral activity

Abstract

Three types of sugar modified pyrimido[4,5-b]indole nucleosides (2′-deoxy-2′-fluororibo-, 2′-deoxy-2′-fluoroarabino- and arabinonucleosides) were synthesized by glycosylation of 4,6-dichloropyrimido[4,5-b]indole followed by modification of sugar moiety and introduction of substituents into position 4 by cross-coupling reactions or nucleophilic substitutions. Some 2′-fluororibo- and 2′-fluoroarabinonucleosides displayed interesting anti-HCV activities (IC50 = 1.6–20 μM) and the latter compounds also some anti-dengue activities (IC50 = 10.8–40 μM).

Graphical abstract: Sugar modified pyrimido[4,5-b]indole nucleosides: synthesis and antiviral activity

Supplementary files

Article information

Article type
Research Article
Submitted
26 Jun 2017
Accepted
24 Aug 2017
First published
25 Aug 2017
This article is Open Access
Creative Commons BY license

Med. Chem. Commun., 2017,8, 1856-1862

Sugar modified pyrimido[4,5-b]indole nucleosides: synthesis and antiviral activity

J. Konč, M. Tichý, R. Pohl, J. Hodek, P. Džubák, M. Hajdúch and M. Hocek, Med. Chem. Commun., 2017, 8, 1856 DOI: 10.1039/C7MD00319F

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