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      2-Substituted 6-(Het)aryl-7-deazapurine Ribonucleosides: Synthesis, Inhibition of Adenosine Kinases, and Antimycobacterial Activity.

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          Abstract

          A series of 6-(hetero)aryl- or 6-methyl-7-deazapurine ribonucleosides bearing a substituent at position 2 (Cl, F, NH2, or CH3) were prepared by cross-coupling reactions at position 6 and functional group transformations at position 2. Cytostatic, antiviral, and antimicrobial activity assays were performed. The title compounds were observed to be potent and selective inhibitors of Mycobacterium tuberculosis adenosine kinase (ADK), but not human ADK; moreover, they were found to be non-cytotoxic. The antimycobacterial activities against M. tuberculosis, however, were only moderate. The reason for this could be due to either poor uptake through the cell wall or to parallel biosynthesis of adenosine monophosphate by the salvage pathway.

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          Author and article information

          Journal
          ChemMedChem
          ChemMedChem
          Wiley
          1860-7187
          1860-7179
          Jun 2015
          : 10
          : 6
          Affiliations
          [1 ] Institute of Organic Chemistry and Biochemistry, Academy of Science Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nám. 2, 16610 Prague 6 (Czech Republic) http://www.uochb.cas.cz/hocekgroup.
          [2 ] Institute of Molecular and Translational Medicine, Palacky University and University Hospital in Olomouc, Faculty of Medicine and Dentistry, Hněvotínská 5, 77515 Olomouc (Czech Republic).
          [3 ] Laboratory for Mycobacterial Diagnostics and Tuberculosis, Regional Institute of Public Health in Ostrava, Partyzánské nám. 7, 70200 Ostrava (Czech Republic).
          [4 ] Institute of Organic Chemistry and Biochemistry, Academy of Science Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nám. 2, 16610 Prague 6 (Czech Republic) http://www.uochb.cas.cz/hocekgroup. hocek@uochb.cas.cz.
          [5 ] Department of Organic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 8, 12843 Prague 2 (Czech Republic). hocek@uochb.cas.cz.
          Article
          10.1002/cmdc.201500081
          25882678
          f0495463-e0cf-4945-bf5b-04788d8fbc04
          History

          cytostatics,nucleosides,purines,pyrrolopyrimidines,antimycobacterial agents

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