Synthesis and biological evaluation of 2′-substituted-4′-selenoribofuranosyl pyrimidines as antitumor agents

Varughese Alexander, Jayoung Song, Jinha Yu, Jung Hee Choi, Jin Hee Kim, Sang Kook Lee, Won Jun Choi, Lak Shin Jeong

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

The 2′-substituted-4′-selenoribofuranosyl pyrimidines 3a-3j were synthesized from D-ribose and assayed for anticancer activity. The 2′-azido and 2′-fluoro groups with a ribo configuration were introduced by the regioselective opening of the O2,2′-anhydronucleosides with sodium azide and (HF)x-pyridine, respectively. Among the compounds tested, only 2′-fluoro derivative 3j was found to exhibit significant anticancer activity, but was much less potent than the corresponding 2′-arabino analogue 2c. This study will provide medicinal chemists with the insight into the identification of structural requirements for the anticancer activity for the developments of biologically active nucleosides.

Original languageEnglish
Pages (from-to)966-972
Number of pages7
JournalArchives of Pharmacal Research
Volume38
Issue number6
DOIs
StatePublished - 20 Sep 2015

Keywords

  • 4′-Selenonucleosides
  • Antitumor activity
  • Azidation
  • Fluorination
  • Regioselective opening

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