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

  • Medchemcomm. 2017 Aug 25;8(9):1856-1862. doi: 10.1039/c7md00319f.
Juraj Konč  1 ,  Michal Tichý  1 ,  Radek Pohl  1 ,  Jan Hodek  1 ,  Petr Džubák  2 ,  Marián Hajdúch  2 ,  Michal Hocek  1  3
Affiliations
  • 1. Institute of Organic Chemistry and Biochemistry , Czech Academy of Sciences , Flemingovo nam. 2 , CZ-16610 Prague 6 , Czech Republic . Email: [email protected].
  • 2. Institute of Molecular and Translational Medicine , Palacky University and University Hospital in Olomouc , Faculty of Medicine and Dentistry , Hněvotínská 5 , CZ-775 15 Olomouc , Czech Republic.
  • 3. Department of Organic Chemistry , Faculty of Science , Charles University in Prague , Hlavova 8 , CZ-12843 Prague 2 , Czech Republic.
PMID: 30108897 DOI: 10.1039/c7md00319f
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).