Discovery of a new template for anticancer agents: 2'-deoxy-2'-fluoro-4'-selenoarabinofuranosyl-cytosine (2'-F-4'-seleno-ara-C)

  • J Med Chem. 2009 Sep 10;52(17):5303-6. doi: 10.1021/jm900852b.
Lak Shin Jeong  1 ,  Dilip K Tosh ,  Won Jun Choi ,  Sang Kook Lee ,  You-Jin Kang ,  Sun Choi ,  Jin Hee Lee ,  Hankil Lee ,  Hyuk Woo Lee ,  Hea Ok Kim
Affiliations
  • 1. Department of Bioinspired Science, Division of Life and Pharmaceutical Sciences, College of Pharmacy, Ewha Womans University, Seoul, Korea. [email protected]
PMID: 19691349 DOI: 10.1021/jm900852b
Abstract

The first synthesis of 2'-deoxy-2'-fluoro-4'-selenoarabinofuranosyl pyrimidines as potent Anticancer agents was accomplished using the DAST fluorination as a key step. It was first revealed that selenium atom participated in the DAST fluorination of 4'-selenonucleosides and that conformational bias induced by bulky selenium acted as a decisive factor in the DAST fluorination. Among compounds tested, 2'-F-4'-seleno-ara-C (4a) exhibited highly potent Anticancer activity in all Cancer cell lines tested and was more potent than ara-C (1).