Synthesis of 2-amino-6-(2-[18F]fluoro-pyridine-4-ylmethoxy)-9-(octyl-β-d-glucosyl)-purine: a novel radioligand for positron emission tomography studies of the O6-methylguanine-DNA methyltransferase (MGMT) status of tumour tissue

Rhenium(i) complexation–dissociation strategy for synthesising fluorine-18 labelled pyridine bidentate radiotracers

“…[8][9][10][11][12] A uorine-18 labelled pyridine tracer designed for the PET imaging of O 6 -methylguanine-DNA methyltransferase (MGMT) status of tumour tissues, 2amino-6-(2-[ 18 F]uoropyridine-4-ylmethoxy)-9-(octyl-b-Dglucosyl)-purine, was also synthesised in only 5% RCY. 13 Given these difficulties associated with uorine-18 labeling pyridinecontaining structures, it was hypothesized that a rhenium(I) activated approach could be a powerful tool towards expanding the scope of such radiotracers. 14 To test this hypothesis, we selected three common bidentate structures throughout our investigation; 1,10-phenanthroline, 2,2 0 -bipyridine and 8hydroxyquinoline.…”

Synthetic Strategies Towards O6-Substituted Guanine Derivatives and their Application in Medicine

“…The idea of glucose conjugation of AGT inhibitors [23] was continued [33] to deliver the pharmaceutical specifically to the tumor tissue via the over-expressed glucose transporters. Radioactive labeling was conducted to prove the concept of targeting in general as well as to quantify the AGT level non-invasively in vivo by positron emission tomography (PET).…”

1,2,3-Triazoles as leaving groups: SNAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles

“…Other methods for the introduction of alkyloxy or aryloxy substituents in the purine structure involve substitution reactions of different leaving groups such as: 1) benzotriazolyloxy group (HOBT) [8,[29][30][31][32]; 2) the alkylimidazolyl group [33,34] and 3) in-situ-generated alkylammonia salts [35][36][37][38]. In 1995, the Robins group demonstrated S N Ar reactions of 6-(1,2,4triazol-4-yl)purine with dimethylamine, sodium methoxide and sodium thiomethoxide [39].…”