Synthesis, Anti-HIV Activity, and Stability Studies of 5′-Phosphorofluoridate Derivatives of AZT

Synthesis of Nucleoside Phosphate and Phosphonate Prodrugs

“…Egron et al 72 tried to improve the anti HIV activity of AZT 5′-fluorophosphate by preparing ( t- Bu-SATE)-prodrug 156 . Starting from H -phosphonate diester 143 (refer to Scheme 44 for preparation), fluorination was achieved using iodine and triethylamine trishydrofluoride.…”

Phosphorofluoridic acid ammonium salts and acids: Synthesis, NMR properties, and application as acid catalysts

“…Filtration and concentration of the reaction mixture gave the desired acids 8 in good to excellent yields. Much less attention has recently been paid to phosphorofluoridic acids with simple carbon skeletons [2,26] found in biologically important molecules [3,10,[27][28][29][30][31].…”

New radiolabelling chemistry: synthesis of phosphorus–[18F]fluorine compounds

“…For example, an AZT analog containing a P-F bond was sufficiently stable to be considered as a potential therapeutic drug. 10,11 (Storage of this compound in aqueous solution for 3 days did not lead to any decomposition. The most 'aggressive' bacterial media studied decomposed it with a 2 h half-life.)…”

“…The most 'aggressive' bacterial media studied decomposed it with a 2 h half-life.) 11 A simple model compound, Dimefox, (tetramethylphosphorodiamidic fluoride; pesticide/cholinesterase inhibitor) was chosen to demonstrate the feasibility of n.c.a. radiofluorination of […”