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Issue 4, 2015
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Synthesis and cytostatic activity of 7-arylsulfanyl-7-deazapurine bases and ribonucleosides

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Abstract

A series of 7-phenylsulfanyl- or 7-(2-thienyl)sulfanyl-7-deazapurine bases bearing diverse substituents at position 6 was prepared through C–H sulfenylation of 6-chloro-7-deazapurine followed by cross-coupling or nucleophilic substitutions. The corresponding ribonucleosides (as thia-analogues of known nucleoside cytostatics) were prepared by glycosylation of 6-chloro-7-arylsulfanyl-7-deazapurines followed by the same transformations at position 6. The 7-thienylsulfanyl-7-deazapurine bases 2b–2h exerted micromolar cytostatic activities, whereas the nucleosides did not show significant biological effects.

Graphical abstract: Synthesis and cytostatic activity of 7-arylsulfanyl-7-deazapurine bases and ribonucleosides

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The article was received on 30 Oct 2014, accepted on 01 Dec 2014 and first published on 02 Dec 2014


Article type: Concise Article
DOI: 10.1039/C4MD00492B
Citation: Med. Chem. Commun., 2015,6, 576-580
  • Open access: Creative Commons BY license
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    Synthesis and cytostatic activity of 7-arylsulfanyl-7-deazapurine bases and ribonucleosides

    M. Klečka, L. P. Slavětínská, E. Tloušťová, P. Džubák, M. Hajdúch and M. Hocek, Med. Chem. Commun., 2015, 6, 576
    DOI: 10.1039/C4MD00492B

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