Fluorinated nucleosides

Abstract

The synthesis and biological activity of deoxyfluoro nucleosides are reviewed.

Selective introduction of a fluorine atom into carbohydrates and a nucleoside by ring-opening fluorination reaction of epoxides

“…In both cases, formation of the regioisomer was not observed. anticancer activities were found [15]. 2'-C-β-Fluoromethyluridine derivative (10) was recently prepared from the corresponding 2'-α-spiroepoxyuridine derivative (9) by the reaction with KHF 2 at 130 ºC for 8h [16].…”

Efficient Radiosynthesis of 2-[18F]Fluoroadenosine: A New Route to 2-[18F]Fluoropurine Nucleosides

“…4 The development of labeling methods for introducing a fluorine-18 atom provides the possibility of access to novel PET probes for in vivo imaging.…”

Design and Synthesis of 4-N-Alkanoyl and 4-N-Alkyl Gemcitabine Analogues Suitable for Positron Emission Tomography

“…8 As such, substitution of hydrogen atoms or hydroxyl groups for fluorine has become a common practice in the search for and design of chemotherapeutically applicable compounds. 8,9 A fluorine atom is a close steric match for a hydrogen atom, still having sufficient electronegativity to effect electronic changes without causing distortion of conformational geometry. 8,9 Moreover, fluorine atoms also have a similar polarity in comparison to a hydroxyl group and as such can act as a hydrogen bond acceptor.…”

“…8,9 A fluorine atom is a close steric match for a hydrogen atom, still having sufficient electronegativity to effect electronic changes without causing distortion of conformational geometry. 8,9 Moreover, fluorine atoms also have a similar polarity in comparison to a hydroxyl group and as such can act as a hydrogen bond acceptor. Since the C-F bond length (1.35Ǻ) so closely resembles that of the C-O bond length of a hydroxyl group (1.43Ǻ), a fluorine atom can serve as an isopolar and isosteric replacement for a hydroxyl group.…”