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.
Bibliographical notePublisher Copyright:
© 2014 The Pharmaceutical Society of Korea.
- Antitumor activity
- Regioselective opening