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

Shin Jeong Lak, Dilip K. Tosh, Jun Choi Won, Kook Lee Sang, You Jin Kang, Sun Choi, Hee Lee Jin, Hankil Lee, Woo Lee Hyuk, Ok Kim Hea

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36 Scopus citations

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).

Original languageEnglish
Pages (from-to)5303-5306
Number of pages4
JournalJournal of Medicinal Chemistry
Volume52
Issue number17
DOIs
StatePublished - 10 Sep 2009

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