Uridine 5-deoxy-5-fluoro

SYNS DEOXYFLUOROURIDINE l-p-d-2 -DEOXYRIBOFURANOSYL-5-FLUOROURACIL FDUR FLOXURIDIN FLOXURIDINE FLUORODEOXY-URIDINE p-5-FLUORO-2 -DEOXYURIDINE 5-FLUORODEOXYURIDINE 5-FLUORO-2-DEOXY-URIDINE 5-FLUORO-2 -DEOXYURIDINE 5-FLUOROURACIL DEOXYRIBOSIDE 5-FLUORO-URACIL-2 -DE0XYRIB0SIDE FLUORURIDINE DEOXYRIBOSE FUDR 5-FUDR NSC-27640 RO 5-0360... 

Perfluoroalkyl)-5 -deoxy-5 -fluoro- and 5-(perfluoroalkyl)-2, 5 -di-deoxy-5 -fluoro-uridines were prepared " from 840 and 834, respectively, using perfluoroalkyl-copper complexes. Among them, 5 -deoxy-5 -fluoro-(846) and 2, 5 -dideoxy-5 -fluoro-5-(perfluoroethyl)uridine (839) were particularly effective against Ehrlich ascites carcinoma. 5-Hydroxyl (847) and 5-amino or 5-alkylamino (5-NHMe, -NHBu, -NHCH2Ph, -morpholino, -piperidino, and -pyrrolo) analogs (848) of 840 were prepared. The a anomer of 5 -deoxy-5 -fluorouridine (840) was also synthesized. "... 

In fluorine-18 chemistry some enzymatic transformations of compounds already labelled with fluorine-18 have been reported the synthesis of 6-[ F] fluoro-L-DOPA from 4-[ F]catechol by jS-tyrosinase [241], the separation of racemic mixtures of p F]fluoroaromatic amino acids by L-amino acylase [242] and the preparation of the coenzyme uridine diphospho-2-deoxy-2-p F]fluoro-a-o-glucose from [ F]FDG-1-phosphate by UDP-glucose pyrophosphorylase [243]. In living nature compounds exhibiting a carbon-fluorine bond are very rare. 

O. Prante, K. Hamacher, H.H. Coenen, Chemo-enzymatic n.c.a. synthesis of the coenzyme uridine diphospho-2-deoxy-2-[ F]fluoro-alpha-D-glucose, J. Label. Compds Radiopharm. 42 (1999) Sill. 

Stoichiometric quantities of uridine diphosphate glucose were used, in the presence of a transfer enzyme, sucrose synthetase, in the soluble state (extraction given). Coupling with modified D-fructose gave sucroses modified on the D-fructosyl group, on the 1 -3-mmol scale. Thus were prepared l -deoxy-l -fluoro- (59%),98 4 -deoxy-4 -fluoro- (16%), and l -azido-l -deoxy-sucrose (15%).71 6-Deoxy-6-fluoro-D-glucose was isomerized to 6-deoxy-6-fluoro-D-fructose with isomerase, and gave 6 -deoxy-6 -fluoro-sucrose.71... 

Condensation of LXVIa (R = p-toluyl) with monomercurithymine (prepared from 1-acetylthymine) produces a mixture of acylated nucleoside anomers (LXVlb and LXVIc, R = thyminyl) which are separated and de-esterified to thymidine and a-thymidine. Similarly, reaction of N-acetylcytosinemercury (LV) with LXVIa (R = p-chlorobenzoyl) yields the a and ft anomers of acylated 2-deoxycytidine which, after separation and deacylation, are converted smoothly to 2-deoxycytidine (LXVlb, R = H, R = cytosinyl) and its a anomer (LXVIc). In like manner, 2-deoxy-5 -fluoro-uridine and -cytidine were synthesized, along with their... 

Analogous reactions have been carried out with uridine (CXI, b series) and with l-jS-D-ribofuranosylthymine (CXI, c series).62 The latter series provided an avenue to the synthesis of 5 -methylcytidine, a nucleoside which is probably identical with that detected by Dunn60 in the ribonucleic acid of wheat germ. The thiation process has also been applied to the synthesis of 5 -fluorocytidine and 2-deoxy-5 -fluorocytidine261 from 5 -fluoro-uridine and 2-deoxy-5 -fluorouridine,209,228 respectively.2618... 

By modifications of known procedures, the following compounds have been prepared l-P-D-arabinofuranosylth3miine,2 -deoxy-5-(trifluoromethyl)-uridine and its a-anomer, a- and p-5-trifluoromethyl-6-aza-2 -deoxyuri-dlnes,l-p-D-arabinofuranosyl-5-fluorouracil,5-fluoro-2 deoxycyti-dine,24 3 -deoxynucleosides of pyrimidines, pyrimidine and purine nucleosides of D-glucuronlc acid, 9-D-mannofuranosyladenlne, 3-P-D-ara-... 

Flox uridine. 2 -Deoxy-5-Jiuorou rid in e l-(2-de-oxy-(J-D-ribofuranosyl)-5-fluorouracil 5 -fluoro -2 -deoxy -... 

Figure 8-3 Metabolic pathway of 5 -deoxy-5-fluoro-uridine and 5-fluorouracil, respectively.

Kawaguchi, T. et al. Control of drug release with a combination of prodrug and polymer matrix antitumor activity and release profiles of 2 ,3 -Diacyl-5-fluoro-2 -deoxy-uridine from poly(3-hydroxybutyrate) microspheres. J. Pharmaceutical Sci. 1992, 87(6), 508-512. 

Routine syntheses of nucleotides have not been covered. Syntheses of more unusual derivatives have included adenosine and uridine 5 -(1-amino)ethylphos-phonate, which are unaffected by alkaline phosphatase, and 5-fluoro-2 -deoxy-uridine 5 V-azidophenylphosphate, used as a photo-affinity label for thymidylate synthetase. 

Deoxy- and 5 -deoxy-5 -halo-derivatives of pseudo-uridine(5- 5-D-ribo-furanosyluracil) have been prepared by conventional methods, with the 5 -fluoro-derivative being prepared from 2, 3 -0-isopropylidene-pseudo-uracil by reaction with 7V,A -diethyl-iV-(2-ehloro-l,l,2-trifluoroethyl)amine as a less conventional fluorinating reagent. Other papers report on the five possible A -monomethyl formycins and the tautomeric equilibrium between the 7- and 8-protonated forms of formycin (25). Further references to antibiotic C-nucleosides are made in Chapter 18. 

In their initial work, these authors reported a poten-tiometric study on the ability of the Zn " " complex of cyclen (80) to interact with the deoxyribonucleotides 2 -deoxyadenosine (dA), 2 -deoxyguanosine (dG), 2 -deoxy-cytidine (dC), 2 -deoxythymidine (dT), uridine (U), and 3 -azido-3 - deoxythymidine (AZT). [Zn(80)] " had a good selectivity for dT, U, AZT, and the related derivatives Ff (ftorafur, 5-fluoro-l-(tetrahydro-2-furyl)uracil), and... 

Fluoro-2 -deoxy-uridine 5 -(4-aminophenyl phosphate) (29) Isolation by afiinity chromatography of thymidylate synthetase 222... 

---