Synthesis and antitumor activity of 1-beta-4-selenoarabinofuranosyl cytosine (4'-seleno-ara-C).

Abstract

4-Seleno analogue of 1-beta-arabinofuranosyl cytosine (ara-C) was synthesized via 4'-selenouridine as a key intermediate, which was easily prepared from D-ribose. The arabino configuration was achieved by chemoselective ring opening of the 2,2'-anhydro-4'-selenouridine. The synthesized 4'-seleno-ara-C showed potent antitumor activity (IC(50) = 1.5 microM) against stomach cancer cells (SNU638).