Discovery of a New Template for Anticancer Agents: 2′-deoxy-2′-fluoro-4′-selenoarabinofuranosyl-cytosine (2′-F-4′-Seleno-ara-C)

Journal of Medicinal Chemistry
2009.0

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).

Knowledge Graph

Similar Paper

Discovery of a New Template for Anticancer Agents: 2′-deoxy-2′-fluoro-4′-selenoarabinofuranosyl-cytosine (2′-F-4′-Seleno-ara-C)
Journal of Medicinal Chemistry 2009.0
Structure–activity relationships of 2′-modified-4′-selenoarabinofuranosyl-pyrimidines as anticancer agents
European Journal of Medicinal Chemistry 2014.0
Synthesis and biological activity of 5-phenylselenenyl-substituted pyrimidine nucleosides
Journal of Medicinal Chemistry 1986.0
Nucleosides and nucleotides. 95. Improved synthesis of 1-(2-azido-2-deoxy-.beta.-D-arabinofuranosyl)cytosine (Cytarazid) and -thymine. Inhibitory spectrum of Cytarazid on the growth of various human tumor cells in vitro
Journal of Medicinal Chemistry 1991.0
Synthesis and Biological Evaluation of Selenium-Containing 4-Anilinoquinazoline Derivatives as Novel Antimitotic Agents
Journal of Medicinal Chemistry 2018.0
Synthesis and evaluation of anti-tumor activities of N4 fatty acyl amino acid derivatives of 1-β-arabinofuranosylcytosine
European Journal of Medicinal Chemistry 2009.0
Nucleosides and nucleotides. 122. 2'-C-Cyano-2'-deoxy-1-.beta.-D-arabinofuranosylcytosine and its derivatives. A new class of nucleoside with a broad antitumor spectrum
Journal of Medicinal Chemistry 1993.0
Nucleosides and nucleotides. 123. Synthesis of 1-(2-deoxy-2-isocyano-.beta.-D-arabinofuranosyl)cytosine and related nucleosides as potential antitumor agents
Journal of Medicinal Chemistry 1993.0
Synthesis and evaluation of diaryl sulfides and diaryl selenide compounds for antitubulin and cytotoxic activity
Bioorganic & Medicinal Chemistry Letters 2013.0
2'-O-Nitro-1-.beta.-D-arabinofuranosylcytosine. A new derivative of 1-.beta.-D-arabinofuranosylcytosine that resists enzymic deamination and has antileukemic activity
Journal of Medicinal Chemistry 1983.0